Diisopropylethylamine → HCID 5272502, compound

HRID 1595276Notes

Reaction equation

HRID 1595276 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][N:11]([CH3:24])[C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[N:16]=1.[OH:25][C:26](=O)[CH2:27][N:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:10][N:11]([CH3:24])[C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:26](=[O:25])[CH2:27][N:28]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[CH:19][CH:18]=2)[N:16]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 105158162-(Benzyl(tert-butoxycarbonyl)amino)acetic acidHCID 18369530HCID 18369530, compound

Product 1

HCID 5272502HCID 5272502, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (4.21 mL, 24.2 mmol) was added to a solution of N,N-dimethyl-4-(4-aminophenyl)-2-thiazolamine (1.77 g, 8.07 mmol, described in the previous section), tert-butyl N-(2-hydroxy-2-oxoethyl)-N-(phenylmethyl)carbamate {2.35 g, 8.87 mmol, described in example 2, section a)} and BOP (3.92 g, 8.87 mmol) in DMF (8 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h then diluted with EtOAc (300 mL). The solution was washed successively with H2O (2×60 mL), saturated aqueous NaHCO3 (60 mL) and brine (60 mL), dried (MgSO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (SiO2, Hex:EtOAc:EtOH, 5:2:1) gave the title compound (3.13 g, 83% yield) as a beige solid: 1H NMR (400 MHz, DMSO-d6) δ9.98, 9.92 (2s, 1 H), 7.80 (d, J=8.4 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 7.26-7.38 (m, 5H), 7.06 (s, 1H), 4.48 (s, 2H), 3.97, 3.86 (2s, 2H), 3.08 (s, 6H), 1.37 (s, 9H); MS (FAB) m/z 467 (MH)+; Anal. Calcd for C25H30N4O3S: C, 64.35; H, 6.48; N, 12.01. Found: C, 64.54; H, 6.56; N, 12.12.

Workup

  1. customat room temperature
  2. washThe solution was washed successively with H2O (2×60 mL), saturated aqueous NaHCO3 (60 mL) and brine (60 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by flash chromatography (SiO2, Hex:EtOAc:EtOH, 5:2:1)

Sources & evidence

ORD record
ord-91e8b0e3409e49038127844eb5a15004
Source dataset
uspto-grants-2001_09
Patent number
US06288091B1

Reaction notes

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