Carbamic acid, 3-azabicyclo[3.1.0]hex-1-YL-, 1,1-dimethylethyl ester → 6-(1-Amino-3-azabicyclo[3.1.0]hexan-3-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525722Notes

Reaction equation

HRID 525722 reaction equation
Cl[C:2]1[C:21]([C:22]2[N:26](C3CCCCO3)[N:25]=[CH:24][CH:23]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[C:33]12([NH:39]C(=O)OC(C)(C)C)[CH2:38][CH:37]1[CH2:36][NH:35][CH2:34]2>>[NH2:39][C:33]12[CH2:38][CH:37]1[CH2:36][N:35]([C:2]1[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:13][CH:14]=3)=[O:7])=[CH:4][N:3]=1)[CH2:34]2

Participants

3

Reactant 2

HCID 21256582Carbamic acid, 3-azabicyclo[3.1.0]hex-1-YL-, 1,1-dimethylethyl esterHCID 867026376-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide

Product 1

HCID 1180447626-(1-Amino-3-azabicyclo[3.1.0]hexan-3-yl)-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 33 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)nicotinamide (Stage 48.2) and tert-butyl 3-azabicyclo[3.1.0]hexan-1-ylcarbamate to afford an off-white foam. HPLC (Condition 4) tR=4.32 min, UPLC-MS (Condition 3) tR=0.79 min, m/z=461.1 [M+H]+.

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-e4bcf612d77c415a8d60de9beb716376
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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