HCID 66830320, compound → HCID 66830262, compound

HRID 1041254Notes

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-8761928a3f9b4dcb995fc88efd0f9aa2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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