Methyl 4-bromobenzoate → HCID 67385716, compound

HRID 912222Notes

Reaction equation

HRID 912222 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.Br[C:42]1[CH:47]=[CH:46][C:45]([S:48]([N:51](C(OC(C)(C)C)=O)[CH2:52][CH2:53][CH2:54][OH:55])(=[O:50])=[O:49])=[CH:44][CH:43]=1.COC(=O)C1C=CC(Br)=CC=1>>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=2)[C:9]2[N:10]=[CH:11][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:42]5[CH:47]=[CH:46][C:45]([S:48]([NH:51][CH2:52][CH2:53][CH2:54][OH:55])(=[O:50])=[O:49])=[CH:44][CH:43]=5)[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:13][N:14]=2)=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 12081Methyl 4-bromobenzoateHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 67384979HCID 67384979, compound

Product 1

HCID 67385716HCID 67385716, compound

Procedure

Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (120 mg) and 4-bromo-N-Boc-N-(3-hydroxy-propyl)-benzenesulfonamide (105 mg) obtained in the same manner as Example 1-D-80 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 4-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-N-(3-hydroxy-propyl)-benzenesulfonamide was obtained, and then the PMB groups were removed according to the above Deprotection method 1, to obtain the desired compound (D-98) as a yellow powder (19 mg, 17%).

Sources & evidence

ORD record
ord-63f53e93218742e28c4bcb22c7d405a7
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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