Dimethylcarbamoyl Chloride → HCID 58529731, compound

HRID 1972836Notes

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

Participants

Reactant 2

HCID 6598Dimethylcarbamoyl Chloride

HCID 58529326HCID 58529326, compound

Product 1

HCID 58529731HCID 58529731, compoundYield 34.1%

Procedure

(5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (75 mg, 0.183 mmol) was reacted with dimethylcarbamoyl chloride (14 uL, 0.192 mmol), according to the procedure of Example 126. The crude product was triturated with 1:1 ether-hexanes to yield (30 mg, 34%) desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.91 (s, 1 H), 7.81 (d, 1 H), 7.59 (s, 1H), 7.45-7.32 (m, 6 H), 7.13 (d, 1 H), 6.65 (s, 1 H), 5.64 (s, 2 H), 3.76 (m, 2 H), 3.42 (m, 3 H), 3.29 (m, 1 H), 2.73 (s, 6 H), 2.31-1.95 (m, 2 H); ES-MS m/z 481.2 [M+H]+, HPLC RT (min) 2.57.

Workup

customThe crude product was triturated with 1:1 ether-hexanes

Sources & evidence

ORD record: ord-fbc09ba1aaf8462188e166699700ab33
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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