Triethylamine → HCID 25159401, compound

HRID 2198271Notes

Reaction equation

HRID 2198271 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[F:16][C:17]1([F:21])[CH2:20][NH:19][CH2:18]1.[C:22]12([C:32](Cl)=[O:33])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[O:23]1)[CH2:29]2.C(N(CC)CC)C>C(#N)C>[F:16][C:17]1([F:21])[CH2:20][N:19]([C:4]([C:3]2[CH:7]=[CH:8][C:9]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:10][C:2]=2[NH:1][C:32]([C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[O:23]2)[CH2:29]3)=[O:33])=[O:6])[CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 27610582-Amino-4-(methylsulfonyl)benzoic acidHCID 75058251HCID 75058251, compound

Product 1

HCID 25159401HCID 25159401, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-4-(methylsulfonyl)benzoic acid (0.25 g) and 3,3-difluoro-azetidine hydrochloride (0.19 g) were reacted according to the method described in Example 332C. The resultant intermediate (0.14 g) was then reacted with 2-oxaadamantane-1-carbonylchloride (1.25 equiv) (prepared from 2-oxaadamantane-1-carboxylic acid and thionyl chloride as in Example 12) and triethylamine (2 equiv) in acetonitrile (10 mL). Evaporation of solvents and flash chromotography over silica gel (10% ethyl acetate/hexane) provided 110 mg of the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.66-2.03 (m, 10H), 2.19 (br s, 2H), 3.25 (s, 3H), 4.43-4.57 (br, 2H), 4.63-4.70 (br, 2H), 7.66 (dd, 1H), 7.82 (d, 1H), 8.79 (d, 1H), 10.76 (s, 1H); MS (ESI+) m/z 455 (M+H)+.

Workup

  1. customEvaporation of solvents and flash chromotography over silica gel (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ff786a91cfa045009f175716e09d12cf
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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