Hydrochloric Acid → HCID 57611885, compound

HRID 1919900Notes

Reaction equation

HRID 1919900 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14](=[O:26])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]([NH2:25])[C:22]([NH2:24])=[O:23])=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C.[CH3:36][C:37](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:38].Cl.C1C[O:64][CH2:63][CH2:62]1>>[C:37]([NH:25][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]([NH:13][C:3]2[CH:4]=[C:5]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:7][C:2]=2[NH:1][C:63](=[O:64])[CH3:62])=[O:26])=[CH:16][CH:17]=1)[C:22]([NH2:24])=[O:23])(=[O:38])[CH3:36]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 24753671HCID 24753671, compound

Product 1

HCID 57611885HCID 57611885, compound

Procedure

N-[2-amino-5-(2-thienyl)phenyl]-4-(1,2-diamino-2-oxoethyl)benzamide (51 mg, 0.086 mmol) and DIPEA (52.4 μL, 0.300 mmol) were suspended in THF (1 mL) and acetic anyhdride (13 μL, 0.138 mmol) was added. The mixture was stirred at room temperature overnight. 2N HCl 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 blue-green solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.89 (s, 1H), 9.71 (s, 1H), 8.55 (d, J=7.8 Hz, 1H), 7.91 (m, 3H), 7.75 (s, 1H), 7.55 (m, 3H), 7.51 (d, J=5.4 Hz, 1H), 7.49 (m, 1H), 7.44 (m, 1H), 7.19 (s, 1H), 7.11 (m, 1H), 5.48 (d, J=7.8 Hz, 1H), 2.07 (s, 3H), 1.89 (s, 3H). MS: cal'd 451 (MH+), exp 451 (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-22af15d21ec34624a9428894737e86ac
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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