Tert-Butylamine → HCID 70976172, compound

HRID 535540Notes

Reaction equation

HRID 535540 reaction equation
[CH3:1][C:2]([NH2:5])([CH3:4])[CH3:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:28]([CH3:32])[C:29](O)=[O:30])=[N:18]2)=[O:15])=[CH:9][CH:8]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C1COCC1>[C:2]([NH:5][C:29](=[O:30])[CH:28]([C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:27])[N:17]([NH:16][C:14](=[O:15])[CH2:13][C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=2)[N:18]=1)[CH3:32])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 70976204HCID 70976204, compound

Product 1

HCID 70976172HCID 70976172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-methylpropan-2-amine (34.1 mg, 0.467 mmol) in THF (5 mL), were added the product from Example 110 (150 mg, 0.389 mmol), triethylamine (0.163 mL, 1.17 mmol), and 1-propanephosphonic acid cyclic anhydride (50% in EtOAc, 0.463 mL, 0.778 mmol). The mixture was stirred at 70° C. for 16 hours, cooled, quenched with 1M NaHCO3 (10 mL), extracted with EtOAc (2×20 mL), dried (Na2SO4-d6), filtered, and concentrated. The residue was purified by chromatography (SiO2, 0-100% of 1/10 MeOH/EtOAc in hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.59 (s, 1H), 8.31 (d, J=7.8, 1H), 8.01-7.97 (m, 2H), 7.93 (s, 1H), 7.87 (ddd, J=8.2, 5.4, 3.0, 1H), 7.41 (s, 4H), 4.24 (q, J=6.8, 1H), 3.68 (s, 2H), 1.39 (d, J=6.9, 3H), 1.23 (s, 9H); MS (ESI+) M/Z 441 (M+H)+.

Workup

  1. temperaturecooled
  2. customquenched with 1M NaHCO3 (10 mL)
  3. extractionextracted with EtOAc (2×20 mL)
  4. customdried (Na2SO4-d6)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (SiO2, 0-100% of 1/10 MeOH/EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc7c79582de04a20bbd250d1b454ccf9
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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