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Diisopropylethylamine → HCID 68681610, compound

HRID 2234519
Notes
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Reaction equation

HRID 2234519 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.[N:13]1([CH2:18][C:19]2([CH2:22][NH2:23])[CH2:21][CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:23][CH2:22][C:19]2([CH2:18][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:20][CH2:21]2)=[O:8])=[C:4]([F:12])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 201514774-Amino-2,5-difluorobenzoic acidHCID 28064766(1-(Pyrrolidin-1-ylmethyl)cyclopropyl)methanamine2×

Product 1

HCID 68681610HCID 68681610, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-amino-2,5-difluoro-benzoic acid (Rare Chemicals GmbH; 700 mg, 4.04 mmol), [1-(pyrrolidin-1-ylmethyl)cyclopropyl]methanamine (Intermediate 33; 655 mg, 4.25 mmol), HATU (1.69 g, 4.44 mmol) and DIPEA (2.1 mL, 12.12 mmol) were combined in DMF (10 mL) and stirred at room temperature for 2 hours. The reaction mixture divided into two portions and each loaded on to an SCX-2 column (20 g) pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) and eluted with 2M ammonia in MeOH. Product containing fractions were evaporated and the residue taken up in DCM and purified on a silica column eluting with a 0-5% gradient of 2M ammonia in MeOH/DCM then 5% 2M ammonia in MeOH/DCM. Fractions containing product were combined and evaporated to yield the title compound as an orange gum which solidified on standing to an orange solid (472 mg, 38%)

Workup

  1. customflushed with MeOH (2 column volumes)
  2. washeluted with 2M ammonia in MeOH
  3. additionProduct containing fractions
  4. customwere evaporated
  5. custompurified on a silica column
  6. washeluting with a 0-5% gradient of 2M ammonia in MeOH/DCM
  7. additionFractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-6217f409257a46539f45298651bac0f7
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709471B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes