4-Hydroxy-3-methylbenzoic acid → HCID 67223773, compound

HRID 2360907Notes

Reaction equation

HRID 2360907 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][C@H:13]12.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[N:12]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([CH3:11])[CH:4]=2)=[O:8])[CH2:17][CH2:16][CH2:15][C@@H:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:24][C@H:13]12

Participants

4

Reactant 3

HCID 681384-Hydroxy-3-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58123900cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

Product 1

HCID 67223773HCID 67223773, compoundYield 35%

Procedure

The title compound is prepared from 4-hydroxy-3-methyl-benzoic acid and cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine following a procedure analogous to that described in Example 1 [2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexa-fluorophosphate is used]. Yield: 35% of theory; LC (method 4): tR=1.92 min; Mass spectrum (ESI+): m/z=313 [M+H]+.

Sources & evidence

ORD record
ord-1c8a93469713491cac0a9a556fe0567c
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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