3-Bromo-4-fluorobenzoic acid → HCID 67385936, compound

HRID 912307Notes

Reaction equation

HRID 912307 reaction equation
BrC1C=C(C=CC=1F)C(O)=O.C(N1CCNCC1)C.Br[C:21]1[CH:22]=[C:23]([C:28]([N:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH3:37])[CH2:32][CH2:31]2)=[O:29])[CH:24]=[CH:25][C:26]=1[F:27].[CH3:38][O:39][C:40]1[CH:77]=[CH:76][C:43]([CH2:44][N:45]([CH2:67][C:68]2[CH:73]=[CH:72][C:71]([O:74][CH3:75])=[CH:70][CH:69]=2)[C:46]2[N:51]=[CH:50][C:49]([C:52]3[C:53]4[CH2:66][CH2:65][NH:64][C:54]=4[N:55]=[C:56]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)[N:57]=3)=[CH:48][N:47]=2)=[CH:42][CH:41]=1>>[CH3:75][O:74][C:71]1[CH:70]=[CH:69][C:68]([CH2:67][N:45]([CH2:44][C:43]2[CH:42]=[CH:41][C:40]([O:39][CH3:38])=[CH:77][CH:76]=2)[C:46]2[N:47]=[CH:48][C:49]([C:52]3[C:53]4[CH2:66][CH2:65][N:64]([C:21]5[CH:22]=[C:23]([C:28]([N:30]6[CH2:35][CH2:34][N:33]([CH2:36][CH3:37])[CH2:32][CH2:31]6)=[O:29])[CH:24]=[CH:25][C:26]=5[F:27])[C:54]=4[N:55]=[C:56]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)[N:57]=3)=[CH:50][N:51]=2)=[CH:73][CH:72]=1

Participants

5

Reactant 4

HCID 705093-Bromo-4-fluorobenzoic acidHCID 791961-EthylpiperazineHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amineHCID 67385652HCID 67385652, compound2×

Product 1

HCID 67385936HCID 67385936, compound

Procedure

Using 3-bromo-4-fluorobenzoic acid (200 mg, 0.913 mmol) and N-ethylpiperazine (232 μl, 1.10 mmol) instead of morpholine, amidation was carried out in the same manner as Example 1-D-16, to obtain a crude product (292 mg) of (3-bromo-4-fluoro-phenyl)-(4-ethyl-piperazin-1-yl)-methanone. Using a crude product (81.8 mg) of the obtained (3-bromo-4-fluoro-phenyl)-(4-ethyl-piperazin-1-yl)-methanone instead of (3-bromo-4-fluoro-phenyl)-morpholin-4-yl-methanone, and bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (70.0 mg, 0.130 mmol), amination was carried out in the same manner as Example 1-D-16, to obtain a crude product of {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]-4-fluoro-phenyl}-(4-ethyl-piperazin-1-yl)-methanone as a yellow solid (152 mg), and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-203) as a yellow powder (48.5 mg, 70%).

Sources & evidence

ORD record
ord-b8551f6525344a0595c8a0e86d936f9d
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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