Methyl 4-bromobenzoate → HCID 67385887, compound

HRID 912185Notes

Reaction equation

HRID 912185 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:41]([O:45][C:46](=[O:58])[N:47]([C:55](=[O:57])[CH3:56])[C:48]1[CH:53]=[CH:52][CH:51]=[C:50](Br)[CH:49]=1)([CH3:44])([CH3:43])[CH3:42].BrC1C=C(NC(=O)C)C=CC=1.C(=O)(OC(C)(C)C)OC(C)(C)C.COC(=O)C1C=CC(Br)=CC=1>C(#N)C.CN(C1C=CN=CC=1)C>[C:41]([O:45][C:46](=[O:58])[N:47]([C:55](=[O:57])[CH3:56])[C:48]1[CH:49]=[CH:50][CH:51]=[C:52]([N:27]2[C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=[C:15]([C:12]4[CH:11]=[N:10][C:9]([N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=5)[CH2:30][C:31]5[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=5)=[N:14][CH:13]=4)[C:16]=3[CH2:29][CH2:28]2)[CH:53]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

8

Reactant 5

HCID 12081Methyl 4-bromobenzoateHCID 12123N-(3-Bromophenyl)acetamideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 67385695HCID 67385695, compound

Product 1

HCID 67385887HCID 67385887, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

From bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (81 mg) and acetyl-(3-bromo-phenyl)-carbamic acid tert-butyl ester (prepared from N-(3-bromo-phenyl)-acetamide and di-t butyl carbonate in acetonitrile in the presence of DMAP, 94 mg) instead of 4-bromobenzoic acid methyl ester in Example 1-D-08, in the same manner as Example 1-D-08, a crude product of acetyl-[3-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-phenyl]-carbamic acid tert-butyl ester was obtained, and then the PMB groups were removed according to Deprotection method 1, to obtain the desired compound (D-45) as a pale yellow powder (5 mg, 8%).

Sources & evidence

ORD record
ord-f94d78e84fb44bd6a1255330f3f2b1ac
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

Loading…