2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethylacetamide → 2-{7-[5-Chloro-4-(3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-4-fluoro-phenylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide

HRID 1687356Notes

Reaction equation

HRID 1687356 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:22])=[C:13]([CH:21]=2)[CH2:14][N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][OH:18])[C:5]([Cl:23])=[CH:4][N:3]=1.[NH2:24][C:25]1[C:41]([O:42][CH3:43])=[CH:40][C:28]2[CH2:29][CH2:30][N:31]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:32][CH2:33][C:27]=2[CH:26]=1>>[Cl:23][C:5]1[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([F:22])=[C:13]([CH2:14][N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][OH:18])[CH:21]=2)=[N:7][C:2]([NH:24][C:25]2[C:41]([O:42][CH3:43])=[CH:40][C:28]3[CH2:29][CH2:30][N:31]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:32][CH2:33][C:27]=3[CH:26]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672635242-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethylacetamideHCID 866339122-{[5-(2,5-Dichloro-pyrimidin-4-ylamino)-2-fluoro-benzyl]-ethyl-amino]-ethanol

Product 1

HCID 668306982-{7-[5-Chloro-4-(3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-4-fluoro-phenylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide

Procedure

The title compound was prepared from 2-{[5-(2,5-Dichloro-pyrimidin-4-ylamino)-2-fluoro-benzyl]-ethyl-amino}-ethanol and 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide in an analogous manner to example 730 (0.047 g, 43%). Mp 71-75° C. LCMS (m/e) 600 (M); 1H-NMR (DMSO, 400 MHz) δ 8.90 (s, 1H), 8.09 (s, 1H), 7.63 (s, 1H), 7.59 (s, 1H), 7.58-7.48 (m, 3H), 7.10-7.02 (t, 1H, J=9.09 Hz), 6.78 (s, 1H), 4.35-4.25 (t, 1H), 3.77 (s, 3H), 3.59 (s, 2H), 3.46-3.45 (q, 2H, J=6.06 Hz), 3.35-3.20 (br, 2H), 3.05 (s, 4H), 2.82 (s, 4H), 2.73 (br, 2H), 2.65-2.52 (m, 4H), 0.98-0.94 (t, 3H, J=7.08 Hz).

Sources & evidence

ORD record
ord-e331329d7e6541338a8651430e986bd7
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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