HCID 67264150, compound → HCID 86634042, compound

HRID 1041469Notes

Reaction equation

HRID 1041469 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([NH2:19])=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1)=[O:7].Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:29]=2[C:30]([NH:32][CH2:33][C:34]#[CH:35])=[O:31])[C:24]([Cl:41])=[CH:23][N:22]=1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([NH:19][C:21]3[N:26]=[C:25]([NH:27][C:28]4[C:29]([C:30](=[O:31])[NH:32][CH2:33][C:34]#[CH:35])=[CH:36][CH:37]=[CH:38][C:39]=4[F:40])[C:24]([Cl:41])=[CH:23][N:22]=3)=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

3

Reactant 2

HCID 67264150HCID 67264150, compoundHCID 866339022-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide

Product 1

HCID 86634042HCID 86634042, compound

Procedure

The title compound was prepared from 3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 2-methoxy-ethyl ester and 2-(2,5-dichloro-pyrimidin-4-ylamino)-3-fluoro-N-prop-2-ynyl-benzamide in an analogous manner to Example 1410. Product isolated as a white foam (70 mg, 44%). LCMS (m/e) 569 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.47-9.36 (m, 1H), 9.24-9.15 (m, 1H), 9.05-8.95 (m, 1H), 8.19 (s, 1H), 7.57-7.41 (m, 3H), 7.33-7.23 (m, 1H), 7.14-7.05 (m, 1H), 6.93 (d, 1H, J=8.7 Hz), 4.23-3.87 (m, 6H), 3.67-3.49 (m, 2H), 3.46-3.37 (m, 1H), 3.36-3.26 (m, 2H), 3.23-3.14 (m, 2H), 3.11 (t, 1H, J=2.4 Hz), 1.97-1.84 (m, 2H).

Sources & evidence

ORD record
ord-53a9eca607de40c08ff981514c789d0e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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