Triethylamine → HCID 58529676, compound

HRID 1972837Notes

Reaction equation

HRID 1972837 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]([CH3:38])[S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>O1CCCC1>[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]([S:34]([N:33]([CH3:38])[CH3:32])(=[O:36])=[O:35])[CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 58529326HCID 58529326, compound

Product 1

HCID 58529676HCID 58529676, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (50 mg, 0.122 mmol) was dissolved in tetrahydrofuran (2 mL). Dimethylsulfamoyl chloride (18 mg, 0.122 mmol) was added to the reaction mixture followed by triethylamine (34 uL, 0.244 mmol). The suspension was stirred at rt overnight. The reaction was concentrated under vacuum. The compound was triturated with 1:1 ether-hexanes to yield desired product (22 mg, 35%). 1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.92 (1s, 1 H), 7.80 (d, 1 H), 7.59 (s, 1 H), 7.20 (m, 3H), 7.35-7.25 (m, 4 H), 7.12 (d, 1 H), 5.64 (s, 2 H), 3.90-3.20 (m, 5H), 2.70-2.05 (m, 8H).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customThe compound was triturated with 1:1 ether-hexanes

Sources & evidence

ORD record
ord-260c0d28fa814bf58fcecac79d291fbe
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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