Salicylic Acid → HCID 50995470, compound

HRID 1772821Notes

Reaction equation

HRID 1772821 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[N:44]1([CH2:50][CH:51]([N:54]2[CH:58]=[C:57]([C:59]3[C:60]4[CH:67]=[CH:66][N:65](COCC[Si](C)(C)C)[C:61]=4[N:62]=[CH:63][N:64]=3)[CH:56]=[N:55]2)[CH2:52][CH3:53])[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C1COCC1>[N:62]1[C:61]2[NH:65][CH:66]=[CH:67][C:60]=2[C:59]([C:57]2[CH:56]=[N:55][N:54]([CH:51]([CH2:52][CH3:53])[CH2:50][N:44]3[CH2:49][CH2:48][N:47]([C:4]([C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[OH:1])=[O:6])[CH2:46][CH2:45]3)[CH:58]=2)=[N:64][CH:63]=1

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58181010HCID 58181010, compound

Product 1

HCID 50995470HCID 50995470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-hydroxybenzoic acid (0.0045 g, 0.033 mmol) in tetrahydrofuran (0.5 mL, 6 mmol) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.012 g, 0.033 mmol) and N,N-diisopropylethylamine (5.7 uL, 0.033 mmol) and mixed for 1 hour until dissolution. The reaction was stirred overnight, then 4-{1-[1-(piperazin-1-ylmethyl)propyl]-1H-pyrazol-4-yl}-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.010 g, 0.022 mmol from step 4 in example 115 and 0.5 mL THF were added. After 0.5 hour, the reaction was purified by LCMS (pH 10) to give 14 mg white solid which was stirred in 1 mL MeOH and 50 microL EDA for 2 hours. The reaction was purified by LCMS (pH 10) to give 2.2 mg white solid. 1H NMR (400 MHz, DMSO): δ 8.64 (1H, s); 8.6 (1H, s); 8.22 (1H, s); 7.55 (1H, d); 7.35 (1H, m); 6.99 (1H, m); 6.93 (1H, m); 688 (1H, m); 6.75 (1H, m); 4.39 (1H, m); 3.5-2.2 (10H, br); 1.78 (2H, m); 0.65 (3H, t). LCMS (M+1); 446.

Workup

  1. additionmixed for 1 hour until dissolution
  2. waitAfter 0.5 hour
  3. customthe reaction was purified by LCMS (pH 10)

Sources & evidence

ORD record
ord-102cf86b6fbc42be9e3da8afe5e06c08
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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