Potassium Carbonate → HCID 178492383, compound

HRID 343237Notes

Reaction equation

HRID 343237 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[C:4](=[O:34])[CH:3]1[CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38](C(C2CSC(=O)N2)=O)[N:37]=1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O.O>[NH:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:36]([CH2:35][CH:3]2[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[O:11])[C:7]3[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=3[N:5]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[C:4]2=[O:34])=[N:37]1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 86753607HCID 86753607, compound

Product 1

HCID 178492383HCID 178492383, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 400 mg (0.556 mmol) of 2-{2,4-Dioxo-3-[1-(2-oxo-thiazolidine-4-carbonyl)-1H-indazol-3-yl methyl]-5-pyridin-3-yl-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl}-N-isopropyl-N-(4-methoxyphenyl) acetamide, prepared as in Example 71 in 10 mL methanol is added 154 mg (1.11 mmol, 2 equiv.) of potassium carbonate. The suspension is stirred for 20 min and diluted with 25 mL EtOAc and 25 mL H2O. The organic phase is washed with H2O (2×25 mL) and then dried (MgSO4), and the solvents removed in vacuo. The resulting amorphous solid is swirled in 10 mL ether until a free flowing white solid is produced. The solid is filtered to give 258 mg of the title compound: mp. 214°-215° C.; [a]25 =+47.2; 1H NMR (CDCl3, 400 MHz) δ8.49 (d, br, 2H), 7.79 (d, 2H, J=8.0), 7.29-7.07 (m, 8H) 6.95-6.85 (m, 4H) 4.94 (m, 1H), 4.38 (d, br, 1H, J=15.6) 4.25-4.14 (m, 2H) 3.82 (s, 3H) 3.77 (m, 1H) 3.60 (dd, 1H, J=6.0, 16.1) 1.02 (t, 6H, J=7.7); low resolution MS (FAB)m/e 589 (MH+).

Workup

  1. washThe organic phase is washed with H2O (2×25 mL)
  2. dry with materialdried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customis produced
  5. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-fd02879010e6421ab4268d424e523ca5
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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