HCID 67263927, compound → HCID 25157924, compound

HRID 1040653Notes

Reaction equation

HRID 1040653 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH3:14])[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:27][C:26]=2[O:37][CH3:38])[C:21]([Cl:39])=[CH:20][N:19]=1.ClC1C(NC2C=CC(N3CCOCC3)=CC=2OC)=NC(NC2C(=O)N(C)C3C=CC=C(OC)C=3CC2)=NC=1>>[Cl:39][C:21]1[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:27][C:26]=2[O:37][CH3:38])=[N:23][C:18]([NH:1][C:2]2[C:7]3[N:8]([CH3:14])[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=3[C:5]([O:15][CH3:16])=[CH:4][CH:3]=2)=[N:19][CH:20]=1

Participants

4

Reactant 3

HCID 67263927HCID 67263927, compoundHCID 86633851(2,5-Dichloropyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amineHCID 86633853HCID 86633853, compound

Product 1

HCID 25157924HCID 25157924, compound

Procedure

Analogous to procedure Example 101b, 9-Amino-6-methoxy-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (40 mg, 0.182 mmol) and (2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-4-morpholin-4-yl-phenyl)-amine (60 mg, 0.165 mmol) were converted to -[5-Chloro-4-(2-methoxy-4-morpholin-4-yl-phenylamino)-pyrimidin-2-ylamino]-6-methoxy-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (32 mg, 37%), purified by ISCO chromatography. MP: 230-232° C. 1H-NMR (CDCl3) δ 8.15 (d, J=8.8 Hz, 1H), 7.96 (s, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.60 (s, 1H), 6.86 (d, J=8.8 Hz, 1H), 6.52 (s, 1H), 6.46 (m, 2H), 3.91 (s, 3H), 3.88 (t, J=4.7 Hz, 4H), 3.85 (s, 3H), 3.16 (s, 3H), 3.14 (t, J=4.6 Hz, 4H), 2.15-2.4 (br m, 5H), 1.84 (br m, 1H); LC/MS (ESI-pos) m/z 539.36 (M+H).

Workup

  1. custompurified by ISCO chromatography

Sources & evidence

ORD record
ord-31c3e4a4a1f24734a673b2158bd38ffb
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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