Triethylamine → HCID 25159519, compound

HRID 2198273Notes

Reaction equation

HRID 2198273 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.Cl.[F:13][C:14]1([F:18])[CH2:17][NH:16][CH2:15]1.[C:19]12([C:29](Cl)=[O:30])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[O:20]1)[CH2:26]2.C(N(CC)CC)C>C(#N)C>[F:13][C:14]1([F:18])[CH2:17][N:16]([C:4]([C:3]2[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=2[NH:1][C:29]([C:19]23[CH2:28][CH:23]4[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]4)[O:20]2)[CH2:26]3)=[O:30])=[O:6])[CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5211422-Amino-6-fluorobenzoic acidHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 75058251HCID 75058251, compound

Product 1

HCID 25159519HCID 25159519, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-6-fluorobenzoic acid (0.25 g) and 3,3-difluoro-azetidine hydrochloride (0.25 g) were reacted according to the method of Example 332C. The resultant intermediate (0.15 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 (20% ethyl acetate/hexane) provided 80 mg of the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.66-2.03 (m, 10H), 2.17 (br s, 2H), 4.36-4.53 (m, 4H), 7.09 (m, 1H), 7.49 (m, 1H), 7.63 (d, 1H), 9.85 (s, 1H); MS (ESI+) m/z 395 (M+H)+.

Workup

  1. customEvaporation of solvents and flash chromotography over silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a6665447154b471b8bc31bfa4e34fb7b
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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