Methanesulfonyl chloride → HCID 67385463, compound

HRID 912253Notes

Reaction equation

HRID 912253 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([C:30]3[CH:31]=[N:32][C:33]([N:36]([CH2:46][C:47]4[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=4)[CH2:37][C:38]4[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=4)=[N:34][CH:35]=3)[C:10]3[CH2:15][CH2:14][N:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH2:23][N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH:17]=4)[C:11]=3[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:55][S:56](Cl)(=[O:58])=[O:57]>>[CH3:55][S:56]([N:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][C:18]2[CH:17]=[C:16]([N:13]3[C:11]4[N:12]=[C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[N:8]=[C:9]([C:30]5[CH:31]=[N:32][C:33]([N:36]([CH2:37][C:38]6[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=6)[CH2:46][C:47]6[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=6)=[N:34][CH:35]=5)[C:10]=4[CH2:15][CH2:14]3)[CH:21]=[CH:20][CH:19]=2)[CH2:25][CH2:26]1)(=[O:58])=[O:57]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67385429HCID 67385429, compound

Product 1

HCID 67385463HCID 67385463, compound

Procedure

In the same manner as Example 1-D-134, using a crude product (80 mg) of 5-{2-morpholin-4-yl-7-[3-(2-piperazin-1-yl-ethyl)-phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}-pyrimidin-2-yl-bis-(4-methoxy-benzyl)-amine obtained in Example 1-D-134 and methanesulfonyl chloride (0.017 ml) instead of acetyl chloride, a crude product of 5-(7-{3-[2-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-phenyl}-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl-bis-(4-methoxy-benzyl)-amine was obtained as a pale yellow solid (82 mg, 93%). Using this crude product (82 mg) of 5-(7-{3-[2-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-phenyl}-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl-bis-(4-methoxy-benzyl)-amine, according to the above Deprotection method 2,5-(7-{3-[2-(4-methanesulfonyl-piperazin-1-yl)-ethyl]-phenyl}-2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine was obtained as a colorless powder (28 mg, 49%).

Sources & evidence

ORD record
ord-50a32dee314a402d9171c80f12bf3598
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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