1-Naphthalenemethanamine → HCID 67267994, compound

HRID 2378083Notes

Reaction equation

HRID 2378083 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-8161ac01e3f34b9b933f63374b8f4e50
Source dataset
uspto-grants-2008_12
Patent number
US07470716B2

Reaction notes

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