Ammonium Chloride → HCID 178505708, compound

HRID 1072088Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:31][CH2:30][CH:29]([C:32]#[N:33])[CH2:28][CH2:27]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[N-:37]=[N+:38]=[N-:39].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4=[C:22]([CH2:25][N:26]5[CH2:27][CH2:28][CH:29]([C:32]6[NH:39][N:38]=[N:37][N:33]=6)[CH2:30][CH2:31]5)[CH:23]=[CH:24][N:20]4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-{4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl }-piperidine-4-carbonitrile (145 mg, 0.3 mmole), sodium azide (59 mg, 3 equiv.) and ammonium chloride (48 mg, 3 equiv.) in DMF (0.6 mL) in a sealed vial was stirred at 100° C. for 20 h. The reaction mixture was cooled to RT, diluted with DCM, washed with water, and dried (Na2SO4). Removal the solvent followed by radial chromatography (2 mm silica gel plate, gradient elution with DCM containing 2 to 7% 2 M NH3 in MeOH) afforded the title compound as a solid (38 mg, 24%); MS: 524 (M+H+); HPLC Ret Time: 1.13 min (Xterra 3.0×50 mm S7 C18 column, 2 min gradient, 5 ml/min).

Workup

temperatureThe reaction mixture was cooled to RT
washwashed with water
dry with materialdried (Na2SO4)
customRemoval the solvent
washfollowed by radial chromatography (2 mm silica gel plate, gradient elution with DCM containing 2 to 7% 2 M NH3 in MeOH)

Sources & evidence

ORD record: ord-6ceed48dc8ba4c36bc24efc51729ba7e
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06908916B2

Reaction notes

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