Acetyl chloride → HCID 58529703, compound

HRID 1972980Notes

Reaction equation

HRID 1972980 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:20]=[CH:21][C:22]4[C:26]([CH:27]=3)=[N:25][N:24]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=4)[C:9](C#N)=[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[CH:35]([N:38](CC)C(C)C)(C)C.[C:44](Cl)(=[O:46])[CH3:45]>C1COCC1.ClCCl>[C:44]([N:14]1[CH2:13][CH2:12][CH:11]([C:10]2[N:6]3[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[C:8]([C:19]3[CH:20]=[CH:21][C:22]4[C:26]([CH:27]=3)=[N:25][N:24]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]=4[C:35]#[N:38])[CH:9]=2)[CH2:16][CH2:15]1)(=[O:46])[CH3:45]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 69302720HCID 69302720, compound

Product 1

HCID 58529703HCID 58529703, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-5-(2-benzyl-2H-indazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazine-6-carbonitrile (50 mg, 0.11 mmol) in THF (2 mL) was added. N,N-diisopropylethylamine (39 μL, 0.22 mmol) followed by acetyl chloride (8.8 μL, 0.11 mmol). The mixture was stirred at rt overnight. The mixture was diluted with dichloromethane (25 mL) and was washed with H2O (20 mL), brine, and was dried (Na2SO4) and concentrated. The crude material was purified by ISCO® chromatography to obtain the desired product (20 mg, 37%). 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.02 (s, 1H), 7.86 (d, 1H), 7.68 (s, 1H), 7.40-7.24 (m, 5H), 7.11 (d, 1H), 5.66 (s, 2H), 4.60-4.56 (m, 1H), 3.00-3.96 (m, 1H), 3.71-3.62 (m, 1H), 3.22-3.18 (m, 1H), 2.66-2.61 (m, 1H), 2.02 (s, 3H), 2.04-1.88 (m, 4H); LC-MS m/z[M+H]+491.3, RT 2.83 min.

Workup

  1. washwas washed with H2O (20 mL), brine
  2. dry with materialwas dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-0d70c0ce43c147c8bbda5855f8075254
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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