Diisopropylethylamine → HCID 58043135, compound

HRID 1035239Notes

Reaction equation

HRID 1035239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:19][CH:18]([O:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=4)[CH2:17]3)=[O:15])=[N:11][N:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.[CH2:36]([C:38]1([OH:42])[CH2:41][NH:40][CH2:39]1)[CH3:37].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:36]([C:38]1([OH:42])[CH2:41][N:40]([CH2:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH:18]3[CH2:19][N:16]([C:14]([C:12]4[O:13][C:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)=[N:10][N:11]=4)=[O:15])[CH2:17]3)=[CH:28][CH:27]=2)[CH2:39]1)[CH3:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 580430894-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeHCID 666534471354792-80-5

Product 1

HCID 58043135HCID 58043135, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 55A (0.20 g, 0.53 mmol) in DCM (10 mL) was added 70A (0.20 g, 0.93 mmol) followed by DIPEA (0.17 mL, 0.95 mmol). The mixture was stirred at RT for 20 min and then sodium triacetoxyborohydride (0.22 g, 1.05 mmol) was added. The mixture was stirred at RT overnight and then washed with an aqueous solution of Na2CO3. The organic solution was filtered through a phase separator and then the solvent was removed by evaporation. The product was purified on a silica gel column using ethyl acetate and then 5% methanol in DCM where the methanol contained 2M ammonia. There was obtained 128 mg (52%) of 70 as a solid. 1H NMR (500 MHz, CDCl3): δ 0.95 (t, 3H), 1.77 (q, 2H), 3.02 (d, 2H), 3.30 (d, 2H), 3.60 (s, 2H), 3.88 (s, 3H), 4.32 (m, 1H), 4.63 (m, 1H), 4.72 (m, 1H), 5.10 (m, 2H), 6.71 (d, 2H), 7.01 (d, 2H), 7.22 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 465 [M+H]+, LC purity: 97%.

Workup

  1. stirringThe mixture was stirred at RT overnight
  2. washwashed with an aqueous solution of Na2CO3
  3. filtrationThe organic solution was filtered through a phase separator
  4. customthe solvent was removed by evaporation
  5. customThe product was purified on a silica gel column

Sources & evidence

ORD record
ord-f881def81b77411f90113ea749c2a3b9
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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