1-Naphthalenemethanamine → HCID 67267994, compound

HRID 602735Notes

Reaction equation

HRID 602735 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[C:22]([O:26][C:27]([NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][N:32]([C:36]2[N:40]([CH2:41][C:42]#[C:43][CH3:44])[C:39]([C:45](O)=[O:46])=[CH:38][N:37]=2)[CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:41]([N:40]1[C:39]([C:45]([NH:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)=[O:46])=[CH:38][N:37]=[C:36]1[N:32]1[CH2:33][CH2:34][CH2:35][CH:30]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:31]1)[C:42]#[C:43][CH3:44]

Participants

7

Reactant 5

HCID 83551-NaphthalenemethanamineHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67268071HCID 67268071, compound

Product 1

HCID 67267994HCID 67267994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.09 ml 1-aminomethylnaphthalene and 0.28 ml ethyldiisopropylamine are added to a solution of 0.20 g 2-(3-tert-butoxycarbonylamino-piperidin-1-yl)-3-(but-2-ynyl)-3H-imidazole-4-carboxylic acid and 0.19 g O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate in 5 ml of dimethylformamide. The solution is stirred for 3 h at ambient temperature and then combined with saturated aqueous potassium carbonate solution. Then the mixture is extracted with ethyl acetate, the organic extracts are dried over sodium sulphate, and the solvent is removed. The residue is purified on silica gel (dichloromethane/methanol 1:0->7:3).

Workup

  1. extractionThen the mixture is extracted with ethyl acetate
  2. dry with materialthe organic extracts are dried over sodium sulphate
  3. customthe solvent is removed
  4. customThe residue is purified on silica gel (dichloromethane/methanol 1:0->7:3)

Sources & evidence

ORD record
ord-ca03b0ce53e84d01810e45d6c75a90d6
Source dataset
uspto-grants-2011_03
Patent number
US07906539B2

Reaction notes

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