Diisopropylethylamine → HCID 58203966, compound

HRID 1190325Notes

Reaction equation

HRID 1190325 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21](NC)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1.[CH:27]([N:30](C(C)C)CC)(C)C.[NH:36]1[CH:40]=[C:39]([C:41]([OH:43])=O)[CH:38]=[N:37]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>O1CCCC1>[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH2:27][NH:30][C:41]([C:39]5[CH:38]=[N:37][NH:36][CH:40]=5)=[O:43])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3015937Pyrazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67050559HCID 67050559, compound

Product 1

HCID 58203966HCID 58203966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[2-(2,2,2-Trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl}-methylamine in tetrahydrofuran was added diisopropylethylamine followed by 1H-pyrazole-4-carboxylic acid and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate. The reaction was stirred at room temperature for about 3 hours. The mixture was partitioned between saturated sodium bicarbonate and ethyl acetate and extracted 3 times with ethyl acetate. The organic layers were combined, dried with MgSO4, and concentrated. The crude was purified by reverse-phase HPLC to give was reacted with to give 106. MS (ESI+) 476.1. 1H NMR (400 MHz, DMSO) δ 13.03 (br, 1H), 8.60 (m, 1H), 8.32-8.22 (m, 2H), 8.07 (s, 2H), 7.15 (dd, J=16.3, 8.3, 1H), 7.00 (s, 1H), 5.84 (q, J=8.7, 2H), 4.43 (d, J=5.9, 2H), 4.36 (t, J=4.9, 2H), 3.45 (t, J=4.9, 2H)

Workup

  1. customThe mixture was partitioned between saturated sodium bicarbonate and ethyl acetate
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified by reverse-phase HPLC
  6. customto give
  7. customwas reacted with

Sources & evidence

ORD record
ord-cbcb2f05114240168351c7d096f41274
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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