Diisopropylethylamine → 736993-54-7

HRID 2054414Notes

Reaction equation

HRID 2054414 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=1.C(N(C(C)C)CC)(C)C.Cl.[CH2:36]([NH:38][C:39]1([C:43]([NH2:45])=[O:44])[CH2:42][NH:41][CH2:40]1)[CH3:37]>COCCOC.O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=[C:2]([N:41]3[CH2:42][C:39]([NH:38][CH2:36][CH3:37])([C:43]([NH2:45])=[O:44])[CH2:40]3)[N:7]2[N:8]=1

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 59655729HCID 59655729, compoundHCID 692108943-(ethylamino)-3-Azetidinecarboxamide hydrochloride

Product 1

HCID 11191162736993-54-7

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred solution of 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 2.00 g, 5.13 mmol) in DME (30 ml) at 23° C. was added diisopropylethylamine (0.940 ml, 5.36 mmol) over 5 minutes. In a separate flask, a solution of 3-ethylaminoazetidine-3-carboxylic acid amide hydrochloride salt (I-2A-1h; 1.16 g, 5.37 mmol) in water (10 ml) was treated with diisopropylethylamine (1.90 ml, 10.8 mmol) over 5 minutes. The aqueous solution was then added to the DME solution over a 10-minute period while maintaining the reaction temperature below 28° C. After 2 hours, water (20 ml) was added over 5 minutes, and an orange solid precipitated from the reaction. The solid product was collected by filtration, washed with additional water, and then air dried by pulling low house vacuum across the sample to afford 2A-1 (2.15 g, 84%) as an off-white solid: +ESI MS (M+1) 496.4; 1H NMR (400 MHz, CD3OD) δ 7.46-7.35 (m, 4H), 7.31 (d, J=7.7 Hz, 2H), 7.21 (d, J=7.7 Hz, 2H), 5.14 (br d, J=8.3 Hz, 1H), 4.77 (br d, J=8.3 Hz, 1H), 4.61 (br d, J=8.3 Hz, 1H), 4.22 (br d, J=8.3 Hz, 1H), 2.54 (q, J=7.1 Hz, 2H), 2.45 (s, 3H), 1.14 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturewhile maintaining the reaction temperature below 28° C
  2. customan orange solid precipitated from the reaction
  3. filtrationThe solid product was collected by filtration
  4. washwashed with additional water
  5. customair dried
  6. customto afford 2A-1 (2.15 g, 84%) as an off-white solid

Sources & evidence

ORD record
ord-192ad04704b3419f8f1b84c2008ae19e
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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