3-(2-Chloroethoxy)aniline → HCID 59513692, compound

HRID 1157551Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[Cl:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>CC(O)C.Cl>[Cl:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[C:36]([NH:37][C:2]2[N:7]=[C:6]([C:8]3[C:9]([C:17]4[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])[CH:20]=[CH:21][CH:22]=4)=[N:10][N:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=34)[CH:5]=[CH:4][N:3]=2)[CH:38]=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 85 °C

Procedure

N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (1.0 g, 2.75 mmol) (see Example 1, Step C) was stirred in (20 mL) of i-PrOH and 3-[(2-chloroethyl)oxy]aniline (0.494 g, 2.89 mmol) was added along with 3 drops of conc. HCl and heated to 85° C. for 18 h. The mixture was filtered hot and washed with i-PrOH to yield the titled product as a yellow solid as the HCl salt (1.2 g, 74% yield). ES-LC/MS m/z 553 (M+H).

Workup

filtrationThe mixture was filtered hot
washwashed with i-PrOH

Sources & evidence

ORD record: ord-a0ea840f344f4955bd646b14c1300925
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807673B2

Reaction notes

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