Hydrochloric Acid → HCID 57905314, compound

HRID 1093136Notes

Reaction equation

HRID 1093136 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:18]4([NH:21][C:22](=[O:31])[C:23](=[O:30])[N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH2:19][CH2:20][CH:15]([CH2:16][CH2:17]4)[CH2:14][N:13]3[C:32](=[O:35])[C:33]=2[OH:34])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[O:47]1[CH2:52][CH2:51][N:50]([S:53]([C:56]2[CH:61]=[CH:60][C:59]([S:62](Cl)(=[O:64])=[O:63])=[CH:58][CH:57]=2)(=[O:55])=[O:54])[CH2:49][CH2:48]1.[O-]CC.[Na+].Cl>ClCCl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:18]4([NH:21][C:22](=[O:31])[C:23]([N:24]5[CH2:25][CH2:26][N:27]([S:62]([C:59]6[CH:60]=[CH:61][C:56]([S:53]([N:50]7[CH2:51][CH2:52][O:47][CH2:48][CH2:49]7)(=[O:55])=[O:54])=[CH:57][CH:58]=6)(=[O:63])=[O:64])[CH2:28][CH2:29]5)=[O:30])[CH2:19][CH2:20][CH:15]([CH2:16][CH2:17]4)[CH2:14][N:13]3[C:32](=[O:35])[C:33]=2[OH:34])=[O:9])=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2723922Sodium ethoxideHCID 27797904-(Morpholine-4-sulfonyl)benzene-1-sulfonyl chlorideHCID 57904939N-(4-Fluorobenzyl)-3-hydroxy-4-oxo-10-((oxo(1-piperazinyl)acetyl)amino)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide

Product 1

HCID 57905314HCID 57905314, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture N-(4-fluorobenzyl)-3-hydroxy-4-oxo-10-((oxo(1-piperazinyl)acetyl)amino)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (25 mg, 0.040 mmol) in dichloromethane (1 mL) was added diisopropyl ethylamine (0.028 mL, 0.160 mmol) followed by 4-(morpholinosulfonyl)benzene-1-sulfonyl chloride (13.00 mg, 0.040 mmol) and the resulting solution stirred at room temperature for 24 h. The mixture was treated with sodium ethoxide (0.015 mL, 0.040 mmol) and stirred at room temperature for 1 h. The reaction was diluted with water and dichloromethane. The aqueous phase was acidified with 1N HCl and the product extracted into the organic phase. The organic phase was concentrated and the residue was triturated with methanol. The white solids were collected by filtration to give the title compound (2.2 mg, 7% yield). (M+H) calcd for C35H41FN7O10S2: 802.23; found: 802.84. 1H NMR (400 MHz, CDCl3) δ: 11.94 (1 H, s), 8.70 (1 H, s), 8.17 (1H, t, J=6.02 Hz), 7.91 (4 H, s), 7.31 (2 H, dd, J=8.41, 5.40 Hz), 6.96 (2 H, t, J=8.66 Hz), 4.51 (2 H, d, J=6.02 Hz), 4.04-4.22 (4 H, m), 3.67-3.80 (4 H, m), 3.44-3.65 (2 H, m), 2.88-3.20 (8 H, m), 2.50-2.67 (2 H, m), 2.46 (1 H, brs), 1.79-2.06 (4 H, m), 1.58-1.77 (2 H, m).

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionthe product extracted into the organic phase
  3. concentrationThe organic phase was concentrated
  4. customthe residue was triturated with methanol
  5. filtrationThe white solids were collected by filtration

Sources & evidence

ORD record
ord-14c2ba15ec1d46ebb4f04e36653ead09
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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