HCID 66830320, compound → HCID 66830262, compound

HRID 1687561Notes

Reaction equation

[NH2:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH3:21][NH:22][C:23]([C:25]1([NH:28][C:29]2[C:34]([Cl:35])=[CH:33][N:32]=[C:31](Cl)[N:30]=2)[CH2:27][CH2:26]1)=[O:24].CNC(C1(NC2C(Cl)=CN=C(NC3C(OC)=CC4CCN(CCOC)CCC=4C=3)N=2)CC1)=O>>[CH3:21][NH:22][C:23]([C:25]1([NH:28][C:29]2[C:34]([Cl:35])=[CH:33][N:32]=[C:31]([NH:1][C:2]3[C:18]([O:19][CH3:20])=[CH:17][C:5]4[CH2:6][CH2:7][N:8]([CH2:11][C:12](=[O:13])[N:14]([CH3:16])[CH3:15])[CH2:9][CH2:10][C:4]=4[CH:3]=3)[N:30]=2)[CH2:27][CH2:26]1)=[O:24]

Participants

Reactant 3

HCID 66830320HCID 66830320, compound

HCID 672635242-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethylacetamide

HCID 86633976HCID 86633976, compound

Product 1

HCID 66830262HCID 66830262, compound

Procedure

Following a procedure similar to Example 258c, 2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide and 1-(2,5-dichloro-pyrimidin-4-ylamino)-cyclopropane carboxylic acid methylamide were converted to 1-{5-chloro-2-[8-methoxy-3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino}-cyclopropane carboxylic acid methylamide as a white solid (28 mg, 19%). MP: 118-125° C.; 1H-NMR (CDCl3) 8.21 (s, 1H), 7.97 (s, 1H), 7.63 (br s, 1H), 6.63 (s, 1H), 6.38 (br s, 1H), 5.62 (s, 1H), 3.87 (s, 3H), 3.27 (s, 2H), 3.16 (s, 3H), 2.97 (s, 3H), 2.91 (m, 2H), 2.85 (m, 2H), 2.78 (d, J=4.8 Hz, 3H), 2.69 (m, 4H), 1.75 (m, 2H), 1.09 (br s, 2H); LC/MS (ESI+): 502.30 (M+H).

Sources & evidence

ORD record: ord-70167bc600a84afcb6c903d9b430c83a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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