2-chloro-N,N-dimethylacetamide → HCID 58529364, compound

HRID 1973011Notes

Reaction equation

HRID 1973011 reaction equation
[NH2:1][C:2]1[N:3]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][C:7]([C:11]1[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:14]3[C:19]=1[C:18]([NH2:20])=[N:17][CH:16]=[N:15]3)=[CH:6]2.Cl[CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38].CCN(C(C)C)C(C)C>C1COCC1.CO>[NH2:20][C:18]1[C:19]2=[C:11]([C:7]3[CH:8]=[CH:9][C:10]4[C:5]([CH:6]=3)=[N:4][N:3]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[C:2]=4[NH2:1])[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38])[CH2:23][CH2:22]3)[N:14]2[N:15]=[CH:16][N:17]=1

Participants

6

Reactant 3

HCID 758862-chloro-N,N-dimethylacetamideHCID 81531DiisopropylethylamineHCID 58529387HCID 58529387, compound

Product 1

HCID 58529364HCID 58529364, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-[3-amino-2-(2-fluorobenzyl)-2H-indazol-6-yl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.1 g, 0.22 mmol) in THF (2 mL) was added 2-chloro-N,N-dimethylacetamide (0.024 g, 0.2 mmol) and DIEA (0.11 g, 0.88 mmol). The mixture was stirred at room temperature for 18 h, diluted with methanol, and concentrated. The crude product was purified by HPLC (10 to 90% CH3CN). 1H NMR (400 MHz, CD2Cl2) δ 7.87 (s, 1 H) 7.58 (d, 1 H) 7.11-7.35 (m, 5 H) 7.01 (d, 1 H) 6.55 (s, 1 H) 5.50-5.55 (m, 4 H) 4.25 (s, 2 H) 2.90-3.30 (m, 11 H) 2.30 (dt, 2 H) 2.10 (d, 2 H) 1.83 (dt, 2 H). LC-MS [M+H]+=542.3, RT=0.31 min.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by HPLC (10 to 90% CH3CN)

Sources & evidence

ORD record
ord-2086be67d4a4489b9ea23d73a5683b95
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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