Hexane → 4-Cyclohexyl-n-{2-[methyl-(1-methyl-pyrrolidin-3-ylmethyl)-amino]-benzooxazol-5-yl}-benzamide

HRID 1174926Notes

Reaction equation

HRID 1174926 reaction equation
[CH3:1][N:2]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:6]=2[N:7]=1.[CH:20]1([C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCCCCC>C(Cl)Cl>[CH:20]1([C:26]2[CH:27]=[CH:28][C:29]([C:30]([NH:12][C:9]3[CH:10]=[CH:11][C:5]4[O:4][C:3]([N:2]([CH3:1])[CH2:13][CH:14]5[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15]5)=[N:7][C:6]=4[CH:8]=3)=[O:31])=[CH:33][CH:34]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 883374-Cyclohexylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57771749Rac-n2-methyl-n2-(1-methyl-pyrrolidin-3-ylmethyl)-benzooxazole-2,5-diamine

Product 1

HCID 115974934-Cyclohexyl-n-{2-[methyl-(1-methyl-pyrrolidin-3-ylmethyl)-amino]-benzooxazol-5-yl}-benzamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine rac-N2-methyl-N2-(1-methyl-pyrrolidin-3-ylmethyl)-benzooxazole-2,5-diamine (0.040 g, 0.154 mmol), 4-cyclohexylbenzoic acid (0.047 g, 0.230 mmol), HATU (0.058 g, 0.154 mmol), polystyrene-bound diisopropylamine (0.385 g, loading: 2.0 to 3.5 mmol/g), and CH2Cl2 (20 mL). Shake the mixture overnight at room temperature. Filter the mixture and wash the polystyrene resin with 1:1 CH2Cl2/MeOH. Subject the mixture to flash column chromatography (12 g column, eluting with 10% 2M NH3 in MeOH/CH2Cl2) to yield a colorless oil. The oil was dissolved in CH2Cl2 and hexane added. The mixture was concentrated and dried under high vacuum to yield the desired product as a white solid (0.034 g, 50%). mass spectrum (m/e): 447.3 (M+1). 1H NMR (400 MHz, CD3OD): δ 7.89-7.85 (m, 2H), 7.71 (d, J=2.0 Hz, 1H), 7.39-7.28 (m, 4H), 3.59 (m, 2H), 3.23 (s, 3H), 2.83-2.58 (m, 6H), 2.39 (s, 3H), 2.13-2.01 (m, 1H), 1.94-1.84 (m, 4H), 1.83-1.76 (m, 1H), 1.67-1.57 (m, 1H), 1.57-1.41 (m, 4H), 1.40-1.28 (m, 1H).

Workup

  1. customthe mixture overnight
  2. customat room temperature
  3. filtrationFilter the mixture
  4. washwash the polystyrene resin with 1:1 CH2Cl2/MeOH
  5. washto flash column chromatography (12 g column, eluting with 10% 2M NH3 in MeOH/CH2Cl2)
  6. customto yield a colorless oil
  7. concentrationThe mixture was concentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-14336d0a322b4502a73769491dbe93f5
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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