Diisopropylethylamine → HCID 57611905, compound

HRID 1919881Notes

Reaction equation

HRID 1919881 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:30]=[C:29]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[CH:28]=[CH:27][C:26]=1[NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:24][C:25]2[CH:30]=[C:29]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[CH:28]=[CH:27][C:26]=2[NH:36][C:37]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:43])=[O:20])=[CH:22][CH:23]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 57611928HCID 57611928, compoundHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 57611905HCID 57611905, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{1-[(tert-butoxycarbonyl)amino]-2-ethoxy-2-oxoethyl}benzoic acid (1.2 g, 3.71 mmol), tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (1.293 g, 4.45 mmol), BOP (2.462 g, 5.57 mmol) and DIPEA (0.972 mL, 5.57 mmol) were stirred in DMF (10 ml) at room temperature for 3 days. Saturated NaHCO3 was added and the products extracted into EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give the desired product as a pale yellow powder. 1H NMR (DMSO-d6, 600 MHz) δ 9.89 (s, 1H), 8.71 (br s, 1H), 7.93 (d, J=8.4 Hz, 2H), 7.87 (d, J=8.4 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.50 (m, 2H), 7.42 (d, J=3.6 Hz, 1H), 7.10 (dd, J=5.4 and 3.6 Hz, 1H), 5.27 (d, J=8.4 Hz, 1H), 4.08 (m, 2H), 1.43 (s, 9H), 1.38 (s, 9H), 1.11 (t, J=7.2 Hz, 3H). MS: cal'd 596 (MH+), exp 440, 484, 496 (MH+).

Workup

  1. extractionthe products extracted into EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-9bf3c42e43f84f078bbf83cb2bbe4724
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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