Triethylamine → HCID 58529951, compound

HRID 1972835Notes

Reaction equation

HRID 1972835 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.[N:32]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.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]([C:38]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[O:39])[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 848104-Morpholinecarbonyl chlorideHCID 58529326HCID 58529326, compound

Product 1

HCID 58529951HCID 58529951, compoundYield 73.2%

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 (75 mg, 0.183 mmol) was dissolved in tetrahydrofuran (2 mL). Morpholine-4-carbonyl chloride (27 mg, 0.183 mmol) was added to the reaction mixture followed by triethylamine (51 uL, 0.366 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 (70 mg, 73%). 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.92 (s, 1 H), 7.79 (d, 1 H), 7.58 (m, 3 H), 7.35-7.32 (m, 4 H), 7.13 (d, 1 H), 6.67 (s, 1 H), 5.64 (s, 2 H), 3.90-2.50 (m, 13 H), 2.50-2.10 (m, 2 H); ES-MS m/z 523.3 [M+H]+, HPLC RT (min) 2.47.

Workup

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

Sources & evidence

ORD record
ord-1f491e772cd2455d982b47a0a5118245
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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