Diisopropylethylamine → HCID 11951475, compound

HRID 1766457Notes

Reaction equation

HRID 1766457 reaction equation
[CH2:1]([NH:8][C:9]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:47][C@@H:48]1[CH2:53][CH2:52][CH2:51][CH2:50][C@H:49]1[OH:54].CCN(C(C)C)C(C)C>CN(C=O)C.C(O)(=O)C>[CH2:1]([NH:8][C:9]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:16][C:12]([C:13]([NH:47][C@@H:48]2[CH2:53][CH2:52][CH2:51][CH2:50][C@H:49]2[OH:54])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21109712HCID 21109712, compound

Product 1

HCID 11951475HCID 11951475, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.2 mg (0.047 mmol) 6-benzylamino-5-(4-chloro-phenyl)-nicotinic acid, 19.6 mg (0.06 mmol) TBTU, 6.9 mg (0.06 mmol) (1R,2R)-2-amino-cyclohexanol and 23 mg (0.18 mmol) DIPEA in DMF was shaken at room temperature over night. Acetic acid was added and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 14.1 mg (55%) of the title compound. MS (m/e): 436.4 (MH+).

Workup

  1. custompurified by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile/water/HCOOH
  4. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-8f37005389dd4439823d9adf947125ce
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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