Trifluoroacetic acid → HCID 25012170, compound

HRID 1013448Notes

Reaction equation

HRID 1013448 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:39][C:40]1[CH:45]=[C:44]([C:46]2[S:47][CH:48]=[CH:49][CH:50]=2)[CH:43]=[CH:42][C:41]=1[NH:51]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>CN(C=O)C>[NH2:51][C:41]1[CH:42]=[CH:43][C:44]([C:46]2[S:47][CH:48]=[CH:49][CH:50]=2)=[CH:45][C:40]=1[NH:39][C:13]([C:12]1[CH:11]=[CH:10][C:9]([P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])=[CH:17][CH:16]=1)=[O:15]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27736884-(Diethoxyphosphoryl)benzoic acidHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 25012170HCID 25012170, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(diethoxyphosphoryl)benzoic acid (commercially available, 50 mg, 0.194 mmol), EDCI (44.6 mg, 0.233 mmol), HOBT (31.5 mg, 0.233 mmol) and tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (67.7 mg, 0.233 mmol) were taken into DMF (0.58 mL) and stirred for 16 h. Approximately 5 mL of TFA was added to the mixture which was stirred for 1 h and concentrated. The product was purified by HPLC (30-90% MeCN in H2O with 0.025% TFA) to afford the requisite product. 1H NMR (DMSO-d6, 600 MHz) δ 9.87 (s, 1H), 8.11 (dd, J=7.9, 3.5 Hz, 2H), 7.83 (dd, J=21.1, 8.2 Hz, 2H), 7.45 (d, J=2.0 Hz, 1H), 7.33 (dd, J=5.0, 0.9 Hz, 1H), 7.29 (dd, J=8.2, 2.0 Hz, 1H), 7.22 (d, J=2.9 Hz, 1H), 7.03 (dd, J=5.0, 3.5 Hz, 1H), 6.79 (d, J=8.5 Hz, 1H), 5.39 (s, 2H), 3.97-4.16 (m, 4H), 1.33 (t, J=7.04 Hz, 6H). MS: cal'd 431 (MH+), exp 431 (MH+).

Workup

  1. stirringwas stirred for 1 h
  2. concentrationconcentrated
  3. customThe product was purified by HPLC (30-90% MeCN in H2O with 0.025% TFA)
  4. customto afford the requisite product

Sources & evidence

ORD record
ord-dc4d97e947014381af4d2eff8b9490de
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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