Diisopropylethylamine → HCID 18771725, compound

HRID 460245Notes

Reaction equation

HRID 460245 reaction equation
C([BH-](CC)CC)C.[Li+].C(N(CC)[C:12]1[N:17]=[C:16]([NH:18][C:19]([NH:21][C:22]2[N:23]=[C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[S:25][CH:26]=2)=[O:20])[C:15](C)=[CH:14][CH:13]=1)C.[CH3:36][CH2:37][N:38]([CH:42](C)C)[CH:39](C)[CH3:40]>C1COCC1>[CH2:37]([N:38]([CH2:42][C:12]1[N:17]=[C:16]([NH:18][C:19]([NH:21][C:22]2[N:23]=[C:24]([CH:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[S:25][CH:26]=2)=[O:20])[CH:15]=[CH:14][CH:13]=1)[CH2:39][CH3:40])[CH3:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 23664628LithiumtriethylborohydrideHCID 69411944HCID 69411944, compound

Product 1

HCID 18771725HCID 18771725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium triethylborohydride (0.84 mL, 0.84 mmol, 1.0 M in THF) was added to a solution of 1-(6-diethylamino-methyl-pyridin-2-yl)-3-(2-pyridin-4-yl-thiazol-4-yl)urea (100 mg, 0.24 mmol, Example 117) and DIEA (63 μL, 0.36 mmol) in THF (5 mL) and the resulting mixture was stirred 6 h at RT. The reaction was quenched via dropwise addition of MeOH and concentrated in vacuo. Purification by preparative HPLC (5–60% CH3CN/H2O) gave a white solid. MS m/z: 389.2 (M+H). Calc'd for C19H28N6OS-388.53.

Workup

  1. customThe reaction was quenched via dropwise addition of MeOH
  2. concentrationconcentrated in vacuo
  3. customPurification by preparative HPLC (5–60% CH3CN/H2O)
  4. customgave a white solid

Sources & evidence

ORD record
ord-0600101c737e408abaa32abaac77c4db
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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