Triethylamine → HCID 25159403, compound

HRID 2198272Notes

Reaction equation

HRID 2198272 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][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>[Cl:11][C:8]1[CH:9]=[CH:10][C: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])=[C:3]([C:4]([N:16]2[CH2:17][C:14]([F:18])([F:13])[CH2:15]2)=[O:6])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 124762-Amino-5-chlorobenzoic acidHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 75058251HCID 75058251, compound

Product 1

HCID 25159403HCID 25159403, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-5-chlorobenzoic acid (0.25 g) and 3,3-difluoro-azetidine hydrochloride (0.24 g) were reacted according to the method of Example 332C. The resultant intermediate (0.16 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 190 mg of the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.66-2.03 (m, 10H), 2.19 (br s, 2H), 4.36-4.81 (br, 4H), 7.54 (dd, 1H), 7.59 (d, 1H), 8.18 (d, 1H), 10.52 (s, 1H); MS (ESI+) m/z 411 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-95ea518ccb824c598332fd19943fcd13
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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