Triethylamine → HCID 58529478, compound

HRID 1972838Notes

Reaction equation

HRID 1972838 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][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>O1CCCC1>[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][N:29]([S:33]([CH3:32])(=[O:35])=[O:34])[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58529326HCID 58529326, compound

Product 1

HCID 58529478HCID 58529478, compoundYield 29.3%

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 (40 mg, 0.098 mmol) was dissolved in tetrahydrofuran (2 mL). Methanesulfonyl chloride (18 mg, 0.127 mmol) was added to the reaction mixture followed by triethylamine (136 uL, 0.977 mmol). The suspension was stirred at rt overnight. The compound was triturated with 1:1 ether-hexanes to yield desired product (14 mg, 29%). 1H NMR (300 MHz, dichloromethane-d2) δ 7.95 (1d, 1 H), 7.80 (1s, 1 H), 7.69-7.97.64 (m, 3 H), 7.27-7.25 (m, 4 H), 7.13 (d, 1 H), 6.54 (s, 1 H) 5.61 (bs, 2 H), 5.61 (bs, 2 H), 5.52 (s, 2H), 4.05-3.90 (m, 2H), 3.60-3.35 (m, 3 H), 2.75 (s, 3 H), 2.45 (m, 1 H), 2.20 (m, 1 H); ES-MS m/z 488.3 [M+H]+, HPLC RT (min) 2.72.

Workup

  1. customThe compound was triturated with 1:1 ether-hexanes

Sources & evidence

ORD record
ord-80a0af3ba0ef4bad883d1883788e9f78
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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