1,2-Dichloroethane → HCID 23657985, compound

HRID 2378994Notes

Reaction equation

HRID 2378994 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9]N=C[C:6]=2[C:5]2[CH2:11][N:12]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:13](=[O:20])[C@H:14]([CH2:16][C:17]([OH:19])=O)[CH2:15][C:4]=2[CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]2[C:37](=[O:38])[NH:36][C:35]3[CH:39]=[CH:40][S:41][C:34]=3[CH:33]=2)[CH2:28][CH2:27]1.[CH:42]1C=CC2N(O)N=NC=2[CH:47]=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:15][C@@H:14]([CH2:16][C:17]([N:26]3[CH2:27][CH2:28][CH:29]([C:32]4[C:37](=[O:38])[NH:36][C:35]5[CH:39]=[CH:40][S:41][C:34]=5[CH:33]=4)[CH2:30][CH2:31]3)=[O:19])[C:13](=[O:20])[N:12]([CH2:21][C:22]([CH3:25])([CH3:23])[CH3:24])[CH2:11][C:5]2=[C:6]2[C:10]=1[NH:9][CH:47]=[CH:42]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59006336HCID 59006336, compoundHCID 59732059HCID 59732059, compound

Product 1

HCID 23657985HCID 23657985, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(4-chloro-9-neopentyl-8-oxo-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl)acetic acid (123 mg, 0.338 mmol), 6-(piperidin-4-yl)thieno[3,2-b]pyridin-5(4H)-one (79 mg, 0.338 mmol), HOBT (56.9 mg, 0.372 mmol), EDC (71.3 mg, 0.372 mmol) in DMF (5 mL) was added DIEA (0.295 mL, 1.690 mmol) at rt, and the mixture was stirred over night. Partial of the solvent was removed under N2 at 60° C., and the residue was purified on reverse phase PrepHPLC to afford the expected product, (S)-6-(1-(2-(7-chloro-2-neopentyl-3-oxo-1,2,3,4,5,8-hexahydroazepino [3,4-e]indol-4-yl)acetyl)piperidin-4-yl)thieno[3,2-b]pyridin-5(4H)-one (113 mg, 57.6%) as a white solid. 1H-NMR (400 MHz, CHLOROFORM-D) δ ppm 0.80 (d, J=6.80 Hz, 11 H) 1.52 (ddd, J=12.46, 8.06, 4.41 Hz, 1H) 1.87-1.96 (m, 1H) 2.00 (s, 1H) 2.38-2.49 (m, 1H) 2.75 (td, J=12.84, 2.01 Hz, 1H) 2.94-3.04 (m, 1H) 3.07-3.18 (m, 4 H) 3.66 (dd, J=13.60, 2.77 Hz, 1H) 3.96-4.06 (m, 1H) 4.23 (s, 1H) 4.61-4.72 (m, 2H) 5.51 (d, J=17.37 Hz, 1H) 7.04 (dd, J=5.29, 2.01 Hz, 1H) 7.22 (s, 1H) 7.70 (dd, J=5.41, 2.14 Hz, 1H) 7.89 (d, J=18.38 Hz, 1H) 8.24 (s, 1H); Mass spec. 580.25 (MH+), Calc. for C30H34ClN5O3S 579.21.

Workup

  1. customPartial of the solvent was removed under N2 at 60° C.
  2. customthe residue was purified on reverse phase PrepHPLC

Sources & evidence

ORD record
ord-1f425a7d5ef54642b44b3026ea0cdc8e
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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