Triethylamine → HCID 69287363, compound

HRID 2225237Notes

Reaction equation

HRID 2225237 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@@H:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][C@H:7]1[CH2:17][CH2:18][CH2:19][CH3:20])=[O:4].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1.C(N(CC)CC)C>C(O)C>[CH2:17]([C@@H:7]1[CH2:8][C@H:9]([NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:10][CH2:11][C@@H:6]1[NH:5][C:3](=[O:4])[CH2:2][NH:1][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2460244,6-DichloroquinazolineHCID 69285591HCID 69285591, compound

Product 1

HCID 69287363HCID 69287363, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Example 2ah, Step 1: A sample of 2-amino-N-((1S,2R,4R)-2-butyl-4-(tert-butylamino)cyclohexyl)acetamide was combined with 4,6-dichloroquinazoline (1.2 equivalents) and triethylamine (1.2 equivalents) in ethanol. The resultant solution was heated at 100° C. in the microwvae for 1 hr. The reaction mixture was concentrated and the residue chromatographed on silica gel (eluting with 2-8% NH4OH/MeOH/CH2Cl2) to give N-((1S,2R,4R)-2-butyl-4-(tert-butylamino)cyclohexyl)-2-(6-chloroquinazolin-4-ylamino)acetamide. MS found: (M+H)+=446.44; 1H NMR (400 MHz, CDCl3) δ(TMS): 0.52-1.77 (m, 25H), 2.36-2.48 (m, 1H), 3.92-4.06 (m, 3H), 6.52-6.63 (M, 1H), 7.37-7.55 (m, 3H), 7.70-7.73 (m, 1H), 7.36-7.41 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue chromatographed on silica gel (eluting with 2-8% NH4OH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-de4241112eae401bae877e910f8d9f3f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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