Acetic Acid → HCID 59254915, compound

HRID 2194997Notes

Reaction equation

HRID 2194997 reaction equation
[C:1](O)(=[O:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]#[C:44][CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:39][C:38]=1[C:51]1[N:60]=[CH:59][C:58]2[CH2:57][CH2:56][C:55]3[N:61]=[C:62]([NH:64][C:65](=[O:67])[CH3:66])[S:63][C:54]=3[C:53]=2[N:52]=1>ClCCl>[C:1]([N:48]1[CH2:47][CH2:46][CH:45]([C:44]#[C:43][C:40]2[CH:41]=[CH:42][C:37]([Cl:36])=[C:38]([C:51]3[N:60]=[CH:59][C:58]4[CH2:57][CH2:56][C:55]5[N:61]=[C:62]([NH:64][C:65](=[O:67])[CH3:66])[S:63][C:54]=5[C:53]=4[N:52]=3)[CH:39]=2)[CH2:50][CH2:49]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59254925HCID 59254925, compound

Product 1

HCID 59254915HCID 59254915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7 μl acetic acid and 50 mg (0.16 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) are placed in 5 mL dichloromethane, combined with 32 μl diisopropylethylamine and stirred for 0.5 hours at ambient temperature. 60 mg (0.13 mmol) N-[8-(2-chloro-5-piperidin-4-ylethynyl-phenyl)-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl]-acetamide (Example 155) are added, then the mixture is stirred for 16 hours at ambient temperature. Then the reaction mixture is extracted with potassium carbonate solution and dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography.

Workup

  1. stirringthe mixture is stirred for 16 hours at ambient temperature
  2. extractionThen the reaction mixture is extracted with potassium carbonate solution and dichloromethane
  3. customThe organic phase is dried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-91c04d4982e04b3591c82a1349e4e174
Source dataset
uspto-grants-2012_12
Patent number
US08334378B2

Reaction notes

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