Diisopropylethylamine → 1-[7-(2-Chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-isopropylaminoazetidine-3-carboxylic Acid Amide

HRID 2054415Notes

Reaction equation

HRID 2054415 reaction equation
Cl.[CH:2]([NH:5][C:6]1([C:10]([NH2:12])=[O:11])[CH2:9][NH:8][CH2:7]1)([CH3:4])[CH3:3].Cl[C:14]1[N:19]2[N:20]=[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[C:22]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[C:18]2[N:17]=[C:16]([CH3:37])[N:15]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:21]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[C:18]2[N:17]=[C:16]([CH3:37])[N:15]=[C:14]([N:8]3[CH2:9][C:6]([NH:5][CH:2]([CH3:4])[CH3:3])([C:10]([NH2:12])=[O:11])[CH2:7]3)[N:19]2[N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 467351463-(Isopropylamino)azetidine-3-carboxamide hydrochlorideHCID 59655729HCID 59655729, compound

Product 1

HCID 113067861-[7-(2-Chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-isopropylaminoazetidine-3-carboxylic Acid Amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-isopropylaminoazetidine-3-carboxylic acid amide hydrochloride salt (I-3A-1c; 72 mg, 0.361 mmol) and 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 102 mg, 0.261 mmol) in methylene chloride (1.3 ml) was added diisopropylethylamine (0.16 ml, 0.91 mmol), dropwise. After stirring for 90 minutes, the reaction was extracted from saturated aqueous NaHCO3 with methylene chloride. The combined extracts were dried (MgSO4), concentrated, in vacuo, and then purified on a Biotage™ Flash 12M column using 0-5% methanol in methylene chloride as eluant. The resultant solid was triturated from methanol and then dried, in vacuo, to afford 3A-1 (104 mg, 78%) as a colorless solid: +ESI MS (M+1) 510.1; 1H NMR (400 MHz, CD2Cl2) δ 7.47-7.34 (m, 6H), 7.21 (d, J=8.7 Hz, 2H), 6.96 (br s, 1H), 5.42 (br s, 1H), 5.22 (br m, 1H), 4.73 (br m, 2H), 4.18 (br m, 1H), 3.11 (septuplet, J=6.2 Hz, 1H), 2.48 (s, 3H), 1.06 (d, J=6.2 Hz, 6H).

Workup

  1. extractionthe reaction was extracted from saturated aqueous NaHCO3 with methylene chloride
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated, in vacuo
  4. custompurified on a Biotage™ Flash 12M column
  5. customThe resultant solid was triturated from methanol
  6. customdried, in vacuo
  7. customto afford 3A-1 (104 mg, 78%) as a colorless solid

Sources & evidence

ORD record
ord-7e69445fa70b4f41a4754b487ba84fad
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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