Diisopropylethylamine → HCID 11949730, compound

HRID 1766506Notes

Reaction equation

HRID 1766506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:17]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([OH:15])=O)=[CH:4][CH:3]=1.Cl.[NH2:24][CH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[OH:32].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([N:17]([CH2:19][CH2:20][O:21][CH3:22])[CH3:18])=[N:10][CH:11]=[C:12]([CH:16]=2)[C:13]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]2[OH:32])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21109703HCID 21109703, compoundHCID 53393211HCID 53393211, compound

Product 1

HCID 11949730HCID 11949730, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 1f, 5-(4-chloro-phenyl)-6-[(2-methoxy-ethyl)-methyl-amino]-nicotinic acid was coupled with cis-2-aminomethyl-1-cyclohexanol hydrochloride using TBTU and N,N-diisopropyl ethyl amine in N,N-dimethylacetamide to give racemic 5-(4-chloro-phenyl)-N-((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-6-[(2-methoxy-ethyl)-methyl-amino]-nicotinamide as an off-white solid. MS (ISP) 432.4 (M+H)+.

Sources & evidence

ORD record
ord-396d8f8a39274c4f833535312b8aedd9
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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