Acetyl chloride → HCID 24999449, compound

HRID 424138Notes

Reaction equation

C(C1C=C([CH2+]=NC2C=C[C:15]([O:16]C3C=CN=C(C(NC)=O)C=3)=[CH:14]C=2F)N(C2C=CC=C(CO)C=2)N=1)(C)(C)C.[C:38]([C:42]1[CH:46]=[C:45]([NH:47][C:48]([NH:50][C:51]2[CH:67]=[CH:66][C:54]([O:55][C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:62]([NH:64][CH3:65])=[O:63])[CH:57]=3)=[CH:53][C:52]=2[F:68])=[O:49])[N:44]([C:69]2[CH:74]=[CH:73][CH:72]=[C:71]([CH2:75][OH:76])[CH:70]=2)[N:43]=1)([CH3:41])([CH3:40])[CH3:39].C(Cl)(=O)C>ClCCl>[C:15]([O:76][CH2:75][C:71]1[CH:72]=[CH:73][CH:74]=[C:69]([N:44]2[C:45]([NH:47][C:48](=[O:49])[NH:50][C:51]3[CH:67]=[CH:66][C:54]([O:55][C:56]4[CH:61]=[CH:60][N:59]=[C:58]([C:62](=[O:63])[NH:64][CH3:65])[CH:57]=4)=[CH:53][C:52]=3[F:68])=[CH:46][C:42]([C:38]([CH3:41])([CH3:39])[CH3:40])=[N:43]2)[CH:70]=1)(=[O:16])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of example 1, (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, (1.00 g, 1.88 mmol) in dichloromethane (15 mL) was added dropwise acetyl chloride (0.15 mL, 2.07 mmol). The reaction mixture was allowed to stir at 0° C. for 1 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The combined organic layer was dried and concentrated. The crude material was purified via column chromatography (CH2Cl2:2M NH3 in MeOH, 97:3) to afford 0.32 g (30%) of the desired product as a white powder. MS m/z 575.1 (M+H)+; Retention time (LC-MS): 3.55 min.

Workup

customThe reaction mixture was quenched with water
extractionextracted with CH2Cl2
customThe combined organic layer was dried
concentrationconcentrated
customThe crude material was purified via column chromatography (CH2Cl2:2M NH3 in MeOH, 97:3)

Sources & evidence

ORD record: ord-acca914e7b1e453d9ccf3a7bc3101d3d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101773B2

Reaction notes

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