Trifluoroacetic acid → 4-{4-[(3R)-3-Methylmorpholin-4-yl]-6-[1-(S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-c]pyridine

HRID 1484050Notes

Reaction equation

HRID 1484050 reaction equation
[CH3:1][C@H:2]1[N:7]([C:8]2[CH:13]=[C:12]([C:14]3([S:17]([CH3:20])(=[NH:19])=[O:18])[CH2:16][CH2:15]3)[N:11]=[C:10]([C:21]3[CH:26]=[N:25][CH:24]=[C:23]4[N:27](C(OC(C)(C)C)=O)[CH:28]=[CH:29][C:22]=34)[N:9]=2)[CH2:6][CH2:5][O:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C@@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:8]1[CH:13]=[C:12]([C:14]2([S:17]([CH3:20])(=[NH:19])=[O:18])[CH2:16][CH2:15]2)[N:11]=[C:10]([C:21]2[CH:26]=[N:25][CH:24]=[C:23]3[NH:27][CH:28]=[CH:29][C:22]=23)[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86660222Tert-butyl 4-(4-((R)-3-methylmorpholino)-6-(1-(S-methylsulfonimidoyl)cyclopropyl)pyrimidin-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Product 1

HCID 547616484-{4-[(3R)-3-Methylmorpholin-4-yl]-6-[1-(S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-c]pyridineYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-((R)-3-methylmorpholino)-6-(1-(S-methylsulfonimidoyl)cyclopropyl)pyrimidin-2-yl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (0.223 g, 0.44 mmol) was added to TFA (5 ml) and DCM (5.00 ml). The resulting solution was stirred at RT for 1 hour. The reaction mixture was evaporated and the residue was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated and the residue was triturated with Et2O to give a solid which was collected by filtration and dried under vacuum to afford the title compound (0.086 g, 48%); 1H NMR (400 MHz, DMSO-d6) 1.29 (3H, d), 1.40-1.60 (3H, m), 1.76 (1H, d), 3.11 (3H, s), 3.12-3.21 (1H, m), 3.53 (1H, t), 3.68 (1H, d), 3.80 (2H, d), 4.01 (1H, d), 4.20 (1H, s), 4.58 (1H, s), 6.95 (1H, d), 7.28 (1H, s), 7.71 (1H, s), 8.83 (1H, s), 9.08 (1H, s), 11.75 (1H, s); m/z: (ES+) MH+, 413.16.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by preparative HPLC
  3. additionFractions containing the desired compound
  4. customwere evaporated
  5. customthe residue was triturated with Et2O
  6. customto give a solid which
  7. filtrationwas collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-79f3e3e19f73455aa9eaff85f9a91dc8
Source dataset
uspto-grants-2016_08
Patent number
US09421213B2

Reaction notes

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