Methanol → HCID 86607819, compound

HRID 2375920Notes

Reaction equation

HRID 2375920 reaction equation
Cl.Cl.Cl.[S:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)=[CH:12][C:7]=2[N:6]=[CH:5]1.C(N(CC)[CH:33]([CH3:35])[CH3:34])(C)C.C([N:42]=[C:43]=[O:44])(C)(C)C.[CH3:45]O>CN(C=O)C>[C:33]([CH:25]1[CH2:24][C:23]([C:21]2[NH:20][C:16]3[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:11]4[CH:10]=[CH:9][C:8]5[S:4][CH:5]=[N:6][C:7]=5[CH:12]=4)[C:15]=3[CH:22]=2)=[CH:28][CH2:27][N:26]1[C:43]([NH2:42])=[O:44])([CH3:34])([CH3:35])[CH3:45]

Participants

6

Reactant 4

HCID 887MethanolHCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 69276870HCID 69276870, compound

Product 1

HCID 86607819HCID 86607819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzothiazol-5-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride (23 mg, 0.050 mmol) and N,N-diisopropylethylamine (0.07 mL, 0.402 mmol) in DMF (2 mL) was stirred at rt for 30 min. tert-Butyl isocyanate (0.012 mL, 0.0 mmol) was added dropwise through a syringe. The resulting mixture was stirred for 1.5 h at rt. MeOH (0.5 mL) was added to quench the reaction. The whole mixture was filtered and purified by HPLC to afford the desired product. 1H-NMR (DMSO-d6, 400 MHz): δ=1.28 (s, 9H), 2.48 (m, 2H), 3.53 (m, 2H), 4.01 (m, 2H), 5.79 (s, 1H), 6.43 (s, br, 1H), 6.84 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 8.35 (d, J=1.2 Hz, 1H), 8.88 (s, 1H), 9.37 (d, J=1.2 Hz, 1H), 9.56 (s, 1H), 11.99 (s, 1H). MS (ES+): m/z 448.08 [MH+]. HPLC: tR=2.60 min (ZQ2000, polar—5 min).

Workup

  1. additionwas added dropwise through a syringe
  2. customto quench
  3. customthe reaction
  4. filtrationThe whole mixture was filtered
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-67ef8a43c91f4b39b3c9c3c68a88dee8
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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