Diisopropylethylamine → HCID 178430822, compound

HRID 1892127Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]1[C:10]2[C:17]([CH3:18])=[CH:16][NH:15][C:11]=2[N:12]=[CH:13][N:14]=1.[Br:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[N:35][C:36]#[N:37])OC2C=CC=CC=2)[CH:23]=[CH:24][CH:25]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Br:19][C:20]1[CH:21]=[C:22]([NH:26]/[C:27](/[N:6]2[CH2:7][CH:2]([CH3:1])[N:3]([C:9]3[C:10]4[C:17]([CH3:18])=[CH:16][NH:15][C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:4][CH:5]2[CH3:8])=[N:35]\[C:36]#[N:37])[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

The dimethyl piperazine from step A (80 mg, 0.32 mmol), phenyl N-3-bromophenyl-N′-cyanocarbamimidate, from Example 5, step A, (100 mg, 0.32 mmol) and N,N-diisopropylethylamine (0.20 ml) were added to isopropanol (10 ml). The mixture was heated at 150° C. for 20 min in a microwave, then concentrated under vacuum. The material was purified prep HPLC (Sunfire C18 30×250 mm column, 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min) to give (E)-N-(3-bromophenyl)-N′-cyano-2,5-dimethyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide (29 mg, 0.062 mmol, 19%).

Workup

concentrationconcentrated under vacuum
customThe material was purified prep HPLC (Sunfire C18 30×250 mm column, 10-100% MeCN:H2O (10 mM NH4OAc), 18 min., 45 ml/min)

Sources & evidence

ORD record: ord-d346fd27a937440cbc56190b7cb9660a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507672B2

Reaction notes

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