Diisopropylethylamine → HCID 121434541, compound

HRID 1486345Notes

Reaction equation

HRID 1486345 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15](O)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:58][CH2:59][C:60]12[CH2:69][CH:64]3[CH2:65][CH:66]([CH2:68][C:62]([C:70]([O:72][CH3:73])=[O:71])([CH2:63]3)[CH2:61]1)[CH2:67]2>CN(C=O)C.C(#N)C.O>[F:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15]([NH:58][CH2:59][C:60]34[CH2:69][CH:64]5[CH2:65][CH:66]([CH2:68][C:62]([C:70]([O:72][CH3:73])=[O:71])([CH2:63]5)[CH2:61]3)[CH2:67]4)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1

Participants

8

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 117858300HCID 117858300, compoundHCID 117859510HCID 117859510, compound

Product 1

HCID 121434541HCID 121434541, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 52 mg of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (75% purity, 0.118 mmol) from Example 4A, 72 mg of HATU (0.188 mmol) and 0.138 ml (0.792 mmol) of N,N-diisopropylethylamine in 0.7 ml of DMF was stirred at RT for 10 min. Subsequently, 53 mg (0.236 mmol) of methyl 3-(aminomethyl)adamantane-1-carboxylate from Example 37A in 0.5 ml of DMF were added and the mixture was stirred at RT overnight. The reaction mixture was admixed with water and acetonitrile and purified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.05% formic acid). 35 mg of the target compound were obtained (53% of theory).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. custompurified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.05% formic acid)

Sources & evidence

ORD record
ord-8c281e583bf4455d9aaef87017a3a98c
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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