Dichloromethane → HCID 23353474, compound

HRID 235130Notes

Reaction equation

HRID 235130 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[C:16]3[N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:26](Cl)(=[O:28])[CH3:27].C(N(CC)CC)C.C(Cl)Cl>O1CCCC1>[C:26]([NH:1][C:2]1[C:3]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[C:16]3[N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23353540HCID 23353540, compound

Product 1

HCID 23353474HCID 23353474, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure of example 30 from the product of example 29 (0.25 g, 0.75 mmol), acetyl chloride (0.045 mL, 0.80 mmol) and triethylamine (0.11 mL, 0.803 mmol) in tetrahydrofuran (8 mL) with stirring at room temperature for 3 hours. The product was isolated by flash chromatography and recrystallization from methylene chloride to yield 0.18g (64%) of the title compound: mp 110°-114° C. (dec.). 1H NMR (DMSOd6) δ 9.47 (s, 1H), 8.65 (d, J=1.5 Hz, 1H), 8.35(s, 1H), 8.03 (dd, J=1.5, 5 Hz, 1H), 7.77-7.70 (m, 2H), 7.53 (dd, J=2, 9 Hz, 1H), 7.46 (d, J=8 Hz, 1H), 7.22 (t, J=8 Hz, 1H), 7.00 (d, J=7.5 Hz, 1H), 6.88 (dd, J=5, 8 Hz, 1H), 3.07 (br s, 4H), 2.63 (br s, 4H), 2.29 (s, 3H), 2.14 (s, 3H). HRMS m/e calculated for C22H25N5O: 375.2054. Observed m/e: 375.2023.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-73e91575c5734abbbcc3b322f62851fa
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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