Dimethylcarbamoyl Chloride → HCID 58529583, compound

HRID 1972884Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:36]=[C:35]5[C:30]([CH2:31][CH2:32][NH:33][CH2:34]5)=[CH:29][CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][N:38]([CH3:42])[C:39](Cl)=[O:40].C(N(CC)CC)C>C1COCC1>[CH3:37][N:38]([CH3:42])[C:39]([N:33]1[CH2:32][CH2:31][C:30]2[C:35](=[CH:36][C:27]([C:19]3[N:20]4[C:25]([C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)=[C:17]([C:12]4[CH:13]=[CH:14][C:15]5[C:10]([CH:11]=4)=[N:9][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:16]=5)[CH:18]=3)=[CH:28][CH:29]=2)[CH2:34]1)=[O:40]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine (150 mg, 0.3 mmol) in THF (2 mL) was added dimethylcarbamyl chloride (44 mg, 0.4 mmol) and triethylamine (64 mg), and the mixture was heated to 40° C. for 4 hours. The mixture was concentrated in vacuo and the residue was dissolved in methanol and purified by preparative HPLC to provide the title compound, 53 mg (31%). 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1 H), 8.05 (d, 2 H), 8.0 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 7.20 (s, 1 H), 5.70 (s, 2 H), 4.4 (m, 2 H), 3.5 (m, 2 H), 2.9 (m, 2 H), 2.8 (s, 6 H); ES-MS m/z 543.47 [M+H]+, HPLC RT (min) 3.16.

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in methanol
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-79a202bc86794a98a49d2007ab9ac659
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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