Formaldehyde → HCID 68278112, compound

HRID 1526906Notes

Reaction equation

HRID 1526906 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:23]=[CH:22][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:24][S:25]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])=[O:26].[CH2:34]=O>C(O)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[O:12])=[CH:22][CH:23]=2)=[N:4][C:3]=1[CH2:24][S:25]([CH:28]1[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 68278059HCID 68278059, compound

Product 1

HCID 68278112HCID 68278112, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 4-[5-methyl-4-[(piperidine-4-sulfonyl)methyl]-1,3-oxazol-2-yl]-N-[2-(pyridin-3-yl)ethyl]benzamide (322 mg, 0.69 mmol, 1.00 equiv) and paraformaldehyde (0.21 g, 10.00 equiv) in formic acid (15 mL) was stirred overnight at 110° C. The resulting mixture was concentrated under vacuum and the crude product (320 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU)): Column, SunFire Prep C18, 19*150 mm Sum; mobile phase, CH3CN/H2O (5% up to 60% in 12 min, up to 100% in 1 min, down to 5% in 1 min); Detector, UV 254 nm, to give 36.5 mg (11%) of 4-[5-methyl-4-[(1-methylpiperidine-4-sulfonyl)methyl]-1,3-oxazol-2-yl]-N-[2-(pyridin-3-yl)ethyl]benzamide as a white solid. LC-MS: (ES, m/z): 483 [M-PH]+, 242. 1HNMR (400 MHz, CD3OD, ppm): δ 8.47 (s, 1H), 8.42-8.40 (s, 1H), 8.08-8.06 (d, 2H), 7.90-7.88 (d, 2H), 7.81-7.79 (d, 1H), 7.42-7.39 (m, 1H), 4.41 (s, 2H), 3.69-3.66 (t, 2H), 3.21-3.06 (m, 1H), 3.06-2.99 (m, 4H), 2.50 (s, 3H), 2.30 (s, 3H), 2.26-2.23 (m, 2H), 2.12-2.06 (m, 2H), 1.95-1.87 (m, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe crude product (320 mg) was purified by Prep-HPLC with the following conditions (1#-Pre-HPLC-001(SHIMADZU))
  3. waitup to 100% in 1 min
  4. waitdown to 5% in 1 min)

Sources & evidence

ORD record
ord-84d2aa7e27f846a2a2b245cf0be7fca3
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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