Triethylamine → HCID 68725919, compound

HRID 1892142Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[N:17][S:18](=[O:21])(=[O:20])[NH2:19])OC2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][C:23]1[C:31]2[C:30]([N:32]3[CH2:37][CH2:36][NH:35][C@@H:34]([CH3:38])[CH2:33]3)=[N:29][CH:28]=[N:27][C:26]=2[NH:25][CH:24]=1.C(N(CC)CC)C>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:35]2[CH2:36][CH2:37][N:32]([C:30]3[C:31]4[C:23]([CH3:22])=[CH:24][NH:25][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:33][C@@H:34]2[CH3:38])=[N:17][S:18](=[O:20])(=[O:21])[NH2:19])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Crude carbamimidate from step B (˜25 mg, 0.068 mmol), (S)-5-methyl-4-(3-methylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine, from Example 1, step B (16 mg, 0.68 mmol), and triethylamine (10 μl, 0.068 mmol) were combined in MeCN (0.5 ml) and heated to 70° C. for 2 hours. The mixture was concentrated and purified by preparative HPLC to afford (S)—N-(3-bromophenyl)-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N′-sulfamoylpiperazine-1-carboximidamide (4 mg, 0.0075 mmol, 11%) as a white solid.

Workup

concentrationThe mixture was concentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-bff76f12ba1b47fb8771f86fa96b557a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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