Diisopropylethylamine → HCID 68811873, compound

HRID 1766467Notes

Reaction equation

HRID 1766467 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([Br:18])=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[OH:27].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>[CH2:1]([O:8][C:9]1[C:17]([Br:18])=[CH:16][C:12]([C:13]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[OH:27])=[O:15])=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 21109715HCID 21109715, compound

Product 1

HCID 68811873HCID 68811873, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 1f, 6-benzyloxy-5-bromo-nicotinic acid was coupled with (1R,2R)-2-amino-cyclohexanol hydrochloride (CAS [5456-63-3]) using TBTU and N,N-diisopropyl ethyl amine in N,N-dimethylacetamide to give 6-benzyloxy-5-bromo-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide as an orange solid.

Sources & evidence

ORD record
ord-1147b46c57854f5cb5b6607c6157ff36
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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