Triethylamine → HCID 67386368, compound

HRID 912237Notes

Reaction equation

HRID 912237 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[S:31][CH:32]=[C:33]([C:35]([OH:37])=O)[N:34]=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:11][N:10]=2)=[CH:5][CH:4]=1.[CH2:49]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[CH3:50].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([CH2:38][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:48][CH:47]=2)[C:9]2[N:10]=[CH:11][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][N:27]([C:30]5[S:31][CH:32]=[C:33]([C:35]([N:54]6[CH2:55][CH2:56][N:51]([CH2:49][CH3:50])[CH2:52][CH2:53]6)=[O:37])[N:34]=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:44][CH:43]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 791961-EthylpiperazineHCID 67385373HCID 67385373, compound

Product 1

HCID 67386368HCID 67386368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-thiazole-4-carboxylic acid (77 mg), N-ethylpiperazine (36 μl), WSCI (68 mg), HOBt (48 mg) and triethylamine (48 μl) were left to act in DMF (3 ml), to obtain a crude product of [2-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-thiazol-4-yl]-(4-ethyl-piperazin-1-yl)-methanone, and then the PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-120) as an ivory powder (38 mg, 63%).

Sources & evidence

ORD record
ord-164dacd1578b4d6c8a0e2f078aa61f0e
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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