2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one → {2-[5-Chloro-2-(3-methoxy-5-methyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-phenoxy}-acetonitrile

HRID 1041511Notes

Reaction equation

HRID 1041511 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[O:11][CH2:12][C:13]#[N:14])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:22]([O:34][CH3:35])=[CH:23][C:24]2[N:30]([CH3:31])[C:29](=[O:32])[O:28][CH2:27][CH2:26][C:25]=2[CH:33]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[O:11][CH2:12][C:13]#[N:14])=[N:7][C:2]([NH:20][C:21]2[C:22]([O:34][CH3:35])=[CH:23][C:24]3[N:30]([CH3:31])[C:29](=[O:32])[O:28][CH2:27][CH2:26][C:25]=3[CH:33]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672646482-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-oneHCID 86633910[2-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrile

Product 1

HCID 66829717{2-[5-Chloro-2-(3-methoxy-5-methyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocyclohepten-2-ylamino)-pyrimidin-4-ylamino]-phenoxy}-acetonitrileYield 50%

Procedure

In an analogous manner to Example 1503, the product was prepared from [2-(2,5-Dichloro-pyrimidin-4-ylamino)-phenoxy]-acetonitrile and 2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product isolated as a white solid (55 mg, 50%). mp: 245-247° C., MS (ESI+): 481 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.40 (d, J=8 Hz, 1H), 8.21 (s, 1H), 8.14 (s, 1H), 7.57 (s, 1H), 7.53 (s, 1H), 7.17-7.07 (dt, 3H), 6.71 (s, 1H), 4.92 (s, 1H), 4.48 (t, J=6 Hz, 2H), 3.93 (s, 3H), 3.41 (s, 3H), 2.85 (t, J=6 Hz, 2H).

Sources & evidence

ORD record
ord-bd75729c76ef4e8b89664428e475f731
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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