Diisopropylethylamine → HCID 90408246, compound

HRID 2275409Notes

Reaction equation

HRID 2275409 reaction equation
[F:1][C:2]1[C:10]2[CH2:9][O:8][B:7]([OH:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[C:58]([NH:62][NH2:63])([CH3:61])([CH3:60])[CH3:59]>CN(C=O)C>[C:58]([NH:62][NH:63][C:12]([C:3]1[CH:4]=[CH:5][C:6]2[B:7]([OH:11])[O:8][CH2:9][C:10]=2[C:2]=1[F:1])=[O:14])([CH3:61])([CH3:60])[CH3:59]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 2724699PyBOPHCID 90407818HCID 90407818, compound

Product 1

HCID 90408246HCID 90408246, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Following the general procedure, mixed together 4-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-5-carboxylic acid (0.500 g, 2.55 mmol), PyBOP (1.34 g, 2.55 mmol), DIEA (0.89 mL, 5.10 mmol) in DMF (6 mL) followed by the addition of tert-butyl hydrazine hydrochloride (0.318 g, 2.55 mmol) and stirred the mixture at 40° C. for 1 h. LCMS showed a main peak at 2.43 with the expected product mass of 267.01 (M+1). After the general work up procedure, the crude dry sample (SKC-07-069, 0.800 g, contains some DMF) was used for the next step without further purification.

Sources & evidence

ORD record
ord-8bc062aef41347c480ed99742e0357ae
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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