Ammonium Chloride → 4-{2-[Bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (2-carbamoyl-ethyl)-amide

HRID 912178Notes

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]([NH:32][CH2:33][CH2:34][C:35]([OH:37])=O)=[O:31])[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.[Cl-].[NH4+].C([N:53](C(C)C)C(C)C)C.C1C=CC2N(O)N=NC=2C=1>O.CN(C=O)C>[C:35]([CH2:34][CH2:33][NH:32][C:30]([N:27]1[C:17]2[N:18]=[C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[N:20]=[C:15]([C:12]3[CH:11]=[N:10][C:9]([N:8]([CH2:38][C:39]4[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=4)[CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:48][CH:47]=4)=[N:14][CH:13]=3)[C:16]=2[CH2:29][CH2:28]1)=[O:31])(=[O:37])[NH2:53]

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF solution (1 ml) of 3-[(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbonyl)-amino]-propionic acid (40 mg) obtained in Step A, ammonium chloride (6.5 mg), N-ethyldiisopropylamine (53 μl), HOBt (8.3 mg) and WSCI (17.6 mg) were added, followed by stirring at 80° C. for 3 hours. To this, water was added and the resulting solid was filtered, to obtain a crude product of the desired compound (33.5 mg, 84%).

Workup

filtrationthe resulting solid was filtered

Sources & evidence

ORD record: ord-f8b2bda0bece47f2af582553464ed0a7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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