Dimethylformamide → HCID 21897610, compound

HRID 1864133Notes

Reaction equation

HRID 1864133 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[CH3:25][N:26]([CH:28]=[O:29])[CH3:27].[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44]3=[N:45][CH:46]=[N:47][C:48]([O:49][CH:50]4[CH2:55]CNC[CH2:51]4)=[C:43]3[CH:42]=[N:41]2)=[CH:36][CH:35]=1)(=[O:33])=[O:32]>C(N(CC)CC)C>[C:43]([C:12]1[N:13]=[CH:14][C:15]([C:28]([N:26]2[CH2:27][CH2:55][CH:50]([O:49][C:48]3[N:47]=[CH:46][N:45]=[C:44]4[N:40]([C:37]5[CH:36]=[CH:35][C:34]([S:31]([CH3:30])(=[O:32])=[O:33])=[CH:39][CH:38]=5)[N:41]=[CH:42][C:43]=34)[CH2:51][CH2:25]2)=[O:29])=[CH:16][CH:11]=1)([CH3:44])([CH3:48])[CH3:42]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 21897610HCID 21897610, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a 20 mL reaction vial was placed a stir bar, 4-t-butylnictinic acid (30 mg), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (60 mg) and DMF (1 mL). The mixture was stirred 10 min at room temperature under N2. 1-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (17.2 mg) and triethylamine (100 μl) was added. After stirred 3 hours at room temperature under N2, the reaction mixture was filtered through a syringe filter. The filtrate was concentrated and purified by HPLC. 1H NMR (DMSO-d6, 400MHz) δ 1.34 (s, 9H), 1.88 (m, 2H), 2.14 (m, 2H), 3.28 (s, 3H), 3.62 (m, 3H), 4.06 (m, 1H), 5.72 (m, 1H), 7.53 (d, 1H), 7.84 (m, 1H), 8.15 (d, 2H), 8.18 (m, 1H), 8.55 (d, 2H), 8.60 (m, 1H), 8.66 (s, 1H), 8.81 (s, 1H). Exact mass calculated for C27H30N6O4S 534.20, found 535.4 (MH+).

Workup

  1. customIn a 20 mL reaction
  2. stirringAfter stirred 3 hours at room temperature under N2
  3. filtrationthe reaction mixture was filtered through a syringe
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-6c0203f1f7154712a5d153fb1d7bf2d6
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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