Dichloromethane → HCID 66873456, compound

HRID 474985Notes

Reaction equation

HRID 474985 reaction equation
[CH3:1][N:2]1[C:11]2[CH2:10][CH2:9][NH:8][CH:7](C(OC(C)(C)C)=O)[CH2:6][C:5]=2[C:4]2[CH:19]=[CH:20][C:21]([N:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:30]=[N:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=4)=[CH:25][C:24]3=[O:39])=[N:22][C:3]1=2.C(Cl)[Cl:41]>Cl.CO.CCOCC>[ClH:41].[CH3:1][N:2]1[C:11]2[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][C:10]=2[C:4]2[CH:19]=[CH:20][C:21]([N:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:30]=[N:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=4)=[CH:25][C:24]3=[O:39])=[N:22][C:3]1=2

Participants

6

Reactant 2

HCID 6344Dichloromethane2×HCID 66873925HCID 66873925, compound

Product 1

HCID 66873456HCID 66873456, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent3×HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

A suspension of tert-butyl 10-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-7,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[3,2-d]azepine-6(5H)-carboxylate (149 mg, 0.276 mmol) in 1.25 M HCl in MeOH (3.0 mL) was stirred under N2 at ambient temperature for 18 h. CH2Cl2 (1.5 mL) was added to the suspension and the resulting solution was stirred at ambient temperature for 18 h. CH2Cl2 (1.0 mL) and 1.25 M HCl in MeOH (1.0 mL) were added to the solution, and the resulting solution was stirred at ambient temperature for 6 h. Additional 1.25 M HCl in MeOH (2.0 mL) was added to the solution, and the resulting solution was stirred for 18 h. The solution was diluted with Et2O, and the resulting solids were collected by filtration to afford the title compound (104 mg, 79%) as a light-yellow powder: mp 308-312° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.21 (d, J=2.0 Hz, 1H), 9.04 (s, 2H), 8.50 (dd, J=8.0, 2.0 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.09-8.05 (m, 2H), 7.47 (d, J=8.0 Hz, 1H), 7.03 (d, J=2.0 Hz, 1H), 6.85 (dd, J=7.5, 2.0 Hz, 1H), 4.49 (s, 2H), 3.80 (s, 3H), 3.49-3.46 (m, 2H), 3.17-3.15 (m, 2H), 2.09-2.07 (m, 2H); ESI MS m/z 440 [M+H]+; HPLC (Method A) 98.1% (AUC), tR=13.4 min.

Workup

  1. stirringthe resulting solution was stirred at ambient temperature for 18 h
  2. stirringthe resulting solution was stirred at ambient temperature for 6 h
  3. stirringthe resulting solution was stirred for 18 h
  4. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-61ba063816354c0da0492e6250580d9d
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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