tert-Butyl piperazine-1-carboxylate → HCID 59244782, compound

HRID 912280Notes

Reaction equation

HRID 912280 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=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[CH:35]=[CH:34][C:33]([CH2:36][CH2:37]C(O)=O)=[CH:32][CH:31]=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)=CC=1.C(O[C:57]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)=[O:58])(C)(C)C>>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:16]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:57]([N:59]5[CH2:60][CH2:61][NH:62][CH2:63][CH2:64]5)=[O:58])=[CH:32][CH:31]=4)[C:17]=3[N:18]=[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:20]=2)=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 59244857HCID 59244857, compound

Product 1

HCID 59244782HCID 59244782, compoundYield 31%

Procedure

Using 3-[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)-phenyl]-propionic acid (61 mg) and piperazine-1-carboxylic acid tert-butyl ester (20 mg) instead of 3-(aminomethyl)pyridine, in the same manner as Step B in Example 1-D-19, 3-[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)-phenyl]-1-(4-tert-butyl-piperazin-1-yl)-propan-1-one was obtained, and further PMB group and BOC group were removed according to the above Deprotection method 2, to obtain the desired compound (D-168) as a pale yellow powder (14 mg, 31%).

Workup

  1. customfurther PMB group and BOC group were removed

Sources & evidence

ORD record
ord-b6d7bb240c4d4b5cbb03058662776b45
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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