Hydrochloric Acid → 1-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochloride

HRID 474976Notes

Reaction equation

HRID 474976 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2>CO>[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66873953tert-butyl 10-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Product 1

HCID 668735841-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.25 M HCl in MeOH (3.0 mL) was added to tert-butyl 10-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (32 mg, 0.060 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated under reduced pressure, the resulting residue was diluted with MeOH (1 mL) and Et2O (10 mL), and the solids were collected by filtration to provide the title compound (31 mg, quant.) as a yellow powder: mp 310-314° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.19 (s, 2H), 9.15 (dd, J=1.0, 1.0 Hz, 1H), 8.41-8.35 (m, 2H), 8.09 (d, J=8.5 Hz, 1H), 8.05 (d, J=7.0 Hz, 1H), 7.43 (d, J=8.5 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.12 (dd, J=7.0, 2.0 Hz, 1H), 3.76 (s, 3H), 3.42-3.40 (m, 2H), 3.36-3.32 (m, 2H), 3.30-3.28 (m, 2H, overlaps with H2O), 3.17 (t, J=6.5 Hz, 2H); ESI MS m/z 440 [M+H]+; HPLC (Method A) 98.83% (AUC), tR=13.9 min.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with MeOH (1 mL) and Et2O (10 mL)
  3. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-85fa752a09314e998c23c3f86391ce2b
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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