O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67064333, compound

HRID 1409220Notes

Reaction equation

HRID 1409220 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH2:16])[CH:8]=2)[CH2:3][CH2:2]1.[CH3:17][O:18][C:19]([C:21]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)[CH2:23][CH2:22]1)=[O:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[C:9]([NH:16][C:28]([C:27]3[CH:26]=[CH:25][C:24]([C:21]4([C:19]([O:18][CH3:17])=[O:20])[CH2:22][CH2:23]4)=[CH:32][CH:31]=3)=[O:29])[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 582073347-Morpholinopyrazolo[1,5-a]pyrimidin-5-amineHCID 588411094-(1-(Methoxycarbonyl)cyclopropyl)benzoic acid

Product 1

HCID 67064333HCID 67064333, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 110 mg, 0.50 mmol) and 4-(1-(methoxycarbonyl)cyclopropyl)benzoic acid (110 mg, 0.50 mmol) were mixed in pyridine (3 ml). TBTU (160 mg, 0.50 mmol) was then added and the mixture was heated to 80° C. for 15 hours. After cooling to room temperature, additional TBTU (53 mg, 0.17 mmol) was added before the heating continued for another 6 hours. After cooling to room temperature, the reaction mixture was quenched with water and was then concentrated to dryness in vacuo. The crude product was purified by preparatory HPLC (35-55% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white powder (72 mg, 35% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.00 (s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.99 (d, J=8.3 Hz, 2H), 7.49 (d, J=8.3 Hz, 2H), 7.41 (s, 1H), 6.38 (d, J=2.3 Hz, 1H), 3.88-3.82 (m, 4H), 3.78-3.70 (m, 4H), 3.57 (s, 3H), 1.56-1.50 (m, 2H), 1.30-1.24 (m, 2H); ESI-MS: m/z 422.4 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was quenched with water
  4. concentrationwas then concentrated to dryness in vacuo
  5. customThe crude product was purified by preparatory HPLC (35-55% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-383353f06d614104979d9b458feb5072
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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